CZ20011466A3 - Deriváty pyrimidinylbenzimidazolu, triazinylbenzimidazolu, anilinpyrimidinu nebo anilintriazinu a je obsahující zemědělské a zahradnické fungicidy - Google Patents
Deriváty pyrimidinylbenzimidazolu, triazinylbenzimidazolu, anilinpyrimidinu nebo anilintriazinu a je obsahující zemědělské a zahradnické fungicidy Download PDFInfo
- Publication number
- CZ20011466A3 CZ20011466A3 CZ20011466A CZ20011466A CZ20011466A3 CZ 20011466 A3 CZ20011466 A3 CZ 20011466A3 CZ 20011466 A CZ20011466 A CZ 20011466A CZ 20011466 A CZ20011466 A CZ 20011466A CZ 20011466 A3 CZ20011466 A3 CZ 20011466A3
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- CZ
- Czechia
- Prior art keywords
- group
- alkoxy
- alkyl
- halogen
- oet
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- WTZRQYJHRXQWTK-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1C1=NC=CC=N1 WTZRQYJHRXQWTK-UHFFFAOYSA-N 0.000 title claims abstract description 13
- -1 triazinyl benzimidazole Chemical compound 0.000 title claims description 44
- 239000000417 fungicide Substances 0.000 title claims description 18
- XQMIGRUKENWSIJ-UHFFFAOYSA-N aniline;pyrimidine Chemical compound C1=CN=CN=C1.NC1=CC=CC=C1 XQMIGRUKENWSIJ-UHFFFAOYSA-N 0.000 title claims 2
- RZQYKMWCITVFBW-UHFFFAOYSA-N aniline;triazine Chemical compound C1=CN=NN=C1.NC1=CC=CC=C1 RZQYKMWCITVFBW-UHFFFAOYSA-N 0.000 title 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 60
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 51
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 49
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 48
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 46
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 43
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 27
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 24
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 21
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 17
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 8
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 262
- 239000000460 chlorine Substances 0.000 description 178
- 150000001875 compounds Chemical class 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000047 product Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000843 powder Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 19
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
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- 239000007864 aqueous solution Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
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- 238000000605 extraction Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000003931 anilides Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 6
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- NGCURIJPLVFJJH-UHFFFAOYSA-N n-phenyltriazin-4-amine Chemical class C=1C=NN=NC=1NC1=CC=CC=C1 NGCURIJPLVFJJH-UHFFFAOYSA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 description 2
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- MWPVZJJSQQLFEB-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-2-methoxybenzimidazole Chemical compound COC1=NC2=CC=CC=C2N1C1=NC(OC)=CC(OC)=N1 MWPVZJJSQQLFEB-UHFFFAOYSA-N 0.000 description 2
- IXVYXVXZJJCRFU-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-5-methylbenzimidazol-2-amine Chemical compound COC1=CC(OC)=NC(N2C3=CC=C(C)C=C3N=C2N)=N1 IXVYXVXZJJCRFU-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UZLVRGBLDHUIDD-UHFFFAOYSA-N 2-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylbenzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 UZLVRGBLDHUIDD-UHFFFAOYSA-N 0.000 description 2
- ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 2
- KXMOBKHNXKAUJD-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 KXMOBKHNXKAUJD-UHFFFAOYSA-N 0.000 description 2
- ZWVBPETWMMFNQP-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)pyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 ZWVBPETWMMFNQP-UHFFFAOYSA-N 0.000 description 2
- RSAWQCDTJIQFAD-UHFFFAOYSA-N 4-chloro-1-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)N)=N1 RSAWQCDTJIQFAD-UHFFFAOYSA-N 0.000 description 2
- MGMBUMDYIHNZKO-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-2-methylbenzimidazole Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2C)=N1 MGMBUMDYIHNZKO-UHFFFAOYSA-N 0.000 description 2
- WFFZSUIFSVKWHZ-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzimidazol-2-amine Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2N)=N1 WFFZSUIFSVKWHZ-UHFFFAOYSA-N 0.000 description 2
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- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
DERIVÁTY PYRIMIDINYLBENZIMIDAZOIJJ, TRIAZINYLBENZIMIDAZOLIJ,
AN1LINPYRIMIDINU NEBO ANIEINTR1AZIMJ A JE OBSAHUJÍCÍ ZEMĚDĚLSKÉ
A ZAHRADNICKÉ FUNGICIDY
OBLAST TECHNIKY
Tento vynález se týká nových derivátů pyrimidinylbenzimidazolu a triazinylbenzimidazolu a zemědělských/zahradnických fungicidů obsahujících uvedené deriváty jako aktivní složku.
DOSAVADNÍ STAV TECHNIKY
Jako látky související s deriváty pyrimidinylbenzimidazolu je zmiňován derivát 4-aminopyrimidinu odhalený jako farmaceutický přípravek v US patentu 5 525 604 a v Evropském patentu č. 640 599, a deriváty pyrimidinu odhalené jako herbicidy v mezinárodní publikaci č. WO94/17 059, ale nebyl učiněn objev týkající zemědělských/zahradnických fungicidů. Francouzský patent č. 1 476 529 odhaluje deriváty benzimidazolyl sulfonamidu s insekticidními a íungicidními aktivitami, ale nebyl učiněn objev týkající se předkládané sloučeniny. Dále jako sloučeniny týkající se derivátů triazinylbenzimidazolu předkládaného vynálezu mohou být zmíněny deriváty triazinu, které byly odhaleny v JP-A-47-36 837, JP-A-4917 677 a Kogyo Kagaku Zassi (Joumal of Industrial Chemistry, vol. 73, č. 5, str. 1000, 1970) jako barvící látky pro textilní zboží, ale nebyl učiněn objev týkající se zemědělských/zahradnických fungicidů. Dále deriváty anilinpyrimidinu jako meziprodukty výroby nebyly proto známy.
Předkládaný vynález poskytuje nové deriváty pyrimidinylbenzimidazolu a triazinylbenzimidazolu a zemědělské/zahradnické fungicidy obsahující uvedené deriváty jako aktivní přísadu.
Předkládající vynálezci provedli extenzivní studie, aby vytvořili nové zemědělské/zahradnické fungicidy a jako výsledek zjistili, že deriváty pyrimidinylbenzimidazolu a triazinylbenzimidazolu předkládaného vynálezu (dále uváděny jako sloučeniny předkládaného vynálezu) jsou nové sloučeniny, které nejsou odhaleny v žádné literatuře a mají vynikající účinek jako zemědělské/zahradnické fungicidy, a předkládaný vynález byl proveden.
PODSTATA VYNÁLEZU
Jmenovitě spočívá předkládaný vynález v derivátech pyrímidinylbenzimidazolu a triazinylbenzimidazolu, reprezentovaných obecným vzorcem I
(1) {kde A je N nebo CR3, každý z R1 a R2, které jsou nezávisle na sobě atom vodíku, halogen, (Ci-Ce) alkylová skupina, (Ca-Cg) alkenylová skupina, (Ca-Cg) alkinylová skupina, (Cs-Ce) cykloalkylová skupina, (Č1-Č4) haloalkylová skupina, (Ci-Q,) alkoxyskupina, (C2-Có) alkenyloxyskupina, (Ca-Ce) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (C1-C4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3-Có) cykloalkyl (C1-C4) alkyloxyskupina, bcnzyloxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (Ci-Ce) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být Substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (C1-C4) alkylkarbonylová skupina, formylová skupina, fénylová skupina, di(C]-C4) alkylaminoskupina, kyano skupina nebo (Ci-Cr,) alkylsulfonyl skupina, R3 je atom vodíku, (Ci-C6) alkylová skupina, (Ci-C6) alkoxyskupina nebo halogen, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Ci-Ce) alkylová skupina, (Cž-Cé) alkenylová skupina, (Cž-Có) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (Ci-Ce) alkylthioskupina, (Ci-Ce) alkylsulfonyl skupina, fenoxyskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (CÍ-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, amino skupina, mono(Ci-C4) alkylaminoskupina, di(Cj-Czí) alkylaminoskupina, anilinová skupina nebo fénylová skupina [uvedená skupina může být substituována halogenem, (Č1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (C]-Cf>) alkylová skupina, (C2-C6) alkenylová skupina, (Ci-Ce) alkinylová skupina, (Ci-Ce) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-Cé) • · · • · · · • · i
• ·
alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fcnylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fcnoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}, deriváty anilinpyrimidinu nebo anilintriazinu, jako jejich meziprodukt, podle obecného vzorce XV
(xv) [kde A je N nebo CR3, každý z R1 a R2, které jsou nezávisle na sobě atom vodíku, halogen, (Ci-Ce) alkylová skupina, (C2-Ce) alkenylová skupina, (Cž-Cg) alkinylová skupina, (C3-C6) cykloalkylová skupina, (C1-C4) haloalkylová skupina, (Ci-Cg) alkoxyskupina, (Ca-Cě) alkenyloxyskupina, (Ců-Cý,) alkínyloxyskupina, (Cs-Cý,) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (CpC4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3-Cf,) cykloalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (Ci-Cf,) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, fenoxyskupína [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (C1-C4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-Ce) alkylsulfonyl skupina, R3 je atom vodíku, (Ci-Q,) alkylová skupina, (Ci-Cg) alkoxyskupina nebo halogen, R5 jé aminoskupina, nitro skupina nebo -NHCOX, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Ci-Ce) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (Cž-Ců) alkenyloxyskupina, (C2-C<,) alkínyloxyskupina, (Ci~C6) alkylthioskupina, (Ci-Ce) alkylsulfonyl ·
• · · · • · í
/| 4 4 4444 4 · 4 4 44 4 · ·· 4 «4 4 «4 444 skupina, fenoxyskupina, (CÍ-C4) alkoxy (CÍ-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, anilinová skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (Ci-Cg) alkylová skupina, (Ci-Cé) alkenylová skupina, (Cž-Cé) alkinylová skupina, (Ci-Ce) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (Cj-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], a n je 0 nebo celé Číslo od 1 do 3}, a zemědělský/zahradnický fungicid obsahující derivát pyrimidinylbenzimidazolu a triazinylbenzimidazolu jako aktivní složku.
Níže budou nyni popsány symboly a termíny použité v předkládané specifikaci.
Halogen je atom fluoru, chloru, bromu nebo jodu.
Zápis jako je (Cj-Ce) označuje, že číslo uhlíku u substituentu, který následuje po tomto zápisu, je v tomto případe od 1 do 6.
(Ci-C6) alkylová skupina je lineární nebo větvená alkylová skupina a je to například methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sek-butyl, terc-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl nebo 3,3-dimethylbutyl.
(C3-C6) cykloalkyl je například cyklopropyl, cyklopentyl nebo cyklohexyl.
(C1-C4) haloalkylová skupina je lineární nebo větvená alkylová skupina substituovaná halogenem a je to například fluoromethyl, chloromethyl. difluoromethyl, dichloromethyl, trifluoromethyl nebo pentafluoroethyl.
(C2-C6) alkenylová skupin je lineární nebo větvená alkenylová skupina a je to například vinyl, 1-propenyl, 2-propenyl, isoprópenyl, 1-butenyl nebo 2-butenyl.
(C2-Ce) alkinylová skupina je lineární nebo větvená alkinylová skupina a je to například ethynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-l-pentynyl.
(Ci-Có) alkox skupina je alkoxyskupina, kde má alkylová skupina výše uvedený význam a je to například methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sek-butoxy, tercbutoxy, n-pentyloxy, isopentyloxy nebo n-hexyloxy.
• · · · • ·
X • · · · · ·· • · · · · · ··
5· ·····«· « 9·· • · · · « «« ·· ♦·· ύ (C2-C6) alkenyloxyskupina je alkenyloxyskupina, kde má alkenylová skupina výše uvedený význam a je to například allyloxy, isopropenyloxy nebo 2-butenyloxy.
(C2-C6) alkinyloxyskupina je alkinyloxyskupina, kde má alkinylová skupina výše uvedený význam a je to například 2-propynyloxy, 2-butynyloxy nebo 3-butynyloxy.
(C3-C6) cykloalkoxyskupina je cykloalkoxyskupina, kde má cykloalkylová skupina výše uvedený význam a je to například cyklopropyloxy, cyklopentyloxy nebo cyklohexyloxy.
(C1-C4) haloalkoxyskupina je haloalkoxyskupina, kde má haloalkylová skupina výše uvedený význam a je to například fluoronethoxy, difluoromethoxy, trifluoromethoxy nebo pentafluoroethoxy.
(Ci-Có) alkylthioskupina je alkylthioskupina, kde má alkylová skupina výše uvedený význam a je to například methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sekbutylthio, terc-butylthio nebo n-hexylthio.
(C3-C6) cyklóalkyl (C1-C4) alkoxyskupina je například cyklopropylmethyloxy, cyklopentylmethyloxy nebo cyklohexylmethyloxy, (C1-C4) alkoxy (C1-C4) alkylová skupina je skupina, kde má alkylová struktura a alkoxy struktura výše uvedené významy a je to například skupina jako methoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl, methoxyethyl nebo butoxyethyl.
(C1-C4) alkoxy (C1-C4) alkyloxyskupina je skupina, kde má alkylová struktura a alkoxy struktura výše uvedené významy a je to například skupina jako methoxymethyloxy, ethoxymethyloxy, isopropoxymethyloxy, pentyloxymethyloxy, methoxyethyloxy nebo butoxyethyloxy.
Kyano (C1-C4) alkyloxyskupina je skupina, kde má alkylová struktura výše uvedený význam a je to například skupina jako kyanometyloxy, kyanoethyloxy nebo kyanopropyloxy.
(C1-C4) alkylkarbonylová skupina je alkylkarbonylová skupina, kde má alkylová struktura výše uvedený význam a je to například skupina jako je acetyl, propionyl, butyryl, isobutyryl, pivaloyl nebo hexanoyl.
(C1-C4) alkoxykarbonylová skupina je alkoxkarbonylová skupina, kde má alkoxylová struktura výše uvedený význam a je to například methoxykarbonyl, ethoxykarbonyl, npropoxykarbonyl, isopropoxykarbonyl, n-butoxykarbonyl, isobutoxykarbonyl, sekbutoxykarbonyl, terc-butoxykarbonyl, n-pentyloxykarbonyl nebo n-hexyloxykarbonyl.
Mono (C1-C4) alkylaminová skupina je monoalkylaminová skupina, kde má alkylová struktura výše uvedený význam a je to například methylamino, ehtylamino, n-propylamino, isopropylamino, n-butylamino, isobuty lamino, sek-butylamino, terc-butylamino nebo nhexylamino.
•· · ·· ···· ·· ··· ·· · · · ·
Di (C1-C4) alkylaminová skupina je například dimethylamino, diethylamino, dípropylamino nebo dibutylamino.
(Ci-Có) alkylsulfonylová skupina je alkylsulfonylová skupina, kde má alkylová struktura výše uvedený význam a je to například methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sek-sulfonyl, terc-butylsulfonyl nebo nhexyl-sulfonyl.
Nyní budou v tabulkách 1 až 35 odhaleny specifické příklady sloučenin podle předkládaného vynálezu reprezentované obecným vzorcem I. Avšak sloučeniny podle předkládaného vynálezu nejsou omezeny pouze na tyto sloučeniny. Zde budou čísla sloučenin uváděna v následném popisu.
Symboly v tabulkách mají následující významy, respektive. Me označuje methyl, Et označuje ethyl, Pr označuje n-propyl, Pr-i označuje isopropyl, Bu označuje n-butyl, Pr-c označuje cyklopropyl, Pn-c označuje cyklopentyl, Ph označuje fenyl a Bn označuje benzyl. Dále Ph(2-Cl) označuje 2-chlorofenyl a Bn(4-Cl) označuje například 4-chlorobenzyl.
7(Tabulka 1)
sloučenina č.
Yn
A R1
R2
| I-l | H | H | CH | OMe | OMe | 167-169 |
| 1-2 | Cl | H | CH | OMe | OMe | 90-91 |
| 1-3 | Br | H | CH | OMe | OMe | 87-90 |
| 1-4 | SMe | H | CH | OMe | OMe | 135-137 |
| 1-5 | SO2Me | H | CH | OMe | OMe | 114-117 |
| 1-6 | Me | H | CH | OMe | OMe | 132-134 |
| 1-7 | Et | H | CH | OMe | OMe | 102-104 |
| 1-8 | Pr | H | CH | OMe | OMe | 107-110 |
| 1-9 | Pr-i | H | CH | OMe | OMe | 70-73 |
| 1-10 | Pr-c | H | CH | OMe | OMe | 62-64 |
| 1-11 | Bu | H | CH | OMe | OMe | |
| 1-12 | Bn | H | CH | OMe | OMe | 94-96 |
| 1-13 | Bn(4-Cl) | H | CH | OMe | OMe | 122-125 |
| 1-14 | Bn,(4-Me) | H | CH | OMe | OMe | 88-90 |
| 1-15 | Bn(4-OMe) | H | CH | OMe | OMe | |
| 1-16 | ch=ch2 | H | CH | OMe | OMe | |
| 1-17 | C=CH | H | CH | OMe | OMe | |
| 1-18 | OMe | H | CH | OMe | OMe | 121-122 |
| 1-19 | OCH2CH=CHj, | H | CH | OMe | OMe | |
| 1-20 | och2c=ch | H | CH | OMe | OMe | |
| 1-21 | och2cf3 | H | CH | OMe | OMe | |
| 1-22 | CH2OEt | H | CH | OMe | OMe | 103-104 |
| 1-23 | CH2C1 | H | CH | OMe | OMe | 132-135 |
| 1-24 | ch2i | H | CH | OMe | OMe | 138-141 |
| 1-25 | cci3 | H | CH | OMe | OMe | 128-131 |
| 1-26 | cf3 | H | CH | OMe | OMe | 79-80 |
| 1-27 | c2f6 | H | CH | OMe | OMe | 97-100 |
| 1-28 | nh2 | H | CH | OMe | OMe |
m.p. : teplota tání RI: refrakční index (Tabulka 2 )
| 1 sloučením . č. | 1 1 X | Yn | A | R1 | R2 | m.D. (°C) nebo (nD ) | |
| 1-29 | NHMe | H | CH | OMe | OMe | 135-138 | |
| 1-30 | N(Me)2 | H | CH | OMe | OMe | 1.5642 | |
| 1-31 | NHPh | H | CH | OMe | OMe | ||
| 1-32 | CO2Et | H | CH | OMe | OMe | ||
| 1-33 | COMe | H | CH | OMe | OMe | ||
| 1-34 | Ph | H | CH | OMe | OMe | 1.6219 | |
| 1-35 | Ph(4-Cl) | H | CH | OMe | OMe | 141-144 | |
| 1-36 | Ph(4-Me) | H | CH | OMe | OMe | ||
| 1-37 | Ph(4-OMe) | H | CH | OMe | OMe | ||
| 1-38 | CN | H | CH | OMe | OMe | 167-168 | |
| 1-39 | no2 | H | CH | OMe | OMe | ||
| 1-40 | H | H | N | OMe | OMe | 148-151 | |
| 1-41 | Cl | H | N | OMe | OMe | 168-171 | |
| 1-42 | Br | H | N | OMe | OMe | ||
| 1-43 | SMe | H | N | OMe | OMe | ||
| 1-44 | SO2Me | H | N | OMe | OMe | ||
| 1-45 | Me | H | N | OMe | OMe | 180-182 | |
| 1-46 | Et | H | N | OMe | OMe | ||
| 1-47 | Pr | H | N | OMe | OMe | 127-128 | |
| 1-48 | Pr-i | H | N | OMe | OMe | 135-141 | |
| 1-49 | Pr-c | H | N | OMe | OMe | ||
| 1-50 | Bu | H | N | OMe | OMe | ||
| 1-51 | Bn | H | N | OMe | OMe | ||
| 1-52 | Bn(4-Cl) | H | N | OMe | OMe | ||
| 1-53 | Bn(4-Me) | H | N | OMe | OMe | ||
| 1-54 | Bn(4-OMe) | H | N | OMe | OMe | ||
| 1-55 | ch=ch2 | H | N | OMe | OMe | ||
| 1-56 | CsCH | H | N | OMe | OMe | ||
| 1-57 | OMe | H | N | OMe | OMe | ||
| 1-58 | OCH2CH=CH2 | H | N | OMe | OMe | ||
| 1-59 | OCH2CsCH | H | N | OMe | OMe | ||
| 1-60 | och2cf3 | H | N | OMe | OMe | ||
| 1-61 | OPh | H | N | OMe | OMe | ||
| 1-62 | CH2OEt | H | N | OMe | OMe |
(Tabulka 3 ) ···♦
| 1-63 | CH2C1 | H | N | OMe | OMe | |
| 1-64 | ch2i | H | N | OMe | OMe | |
| 1-65 | CC13 | H | N | OMe | OMe | |
| 1-66 | cf3 | H | N | OMe | OMe | 143-146 |
| 1-67 | c2f5 | H | N | OMe | OMe | |
| 1-68 | nh2 | H | N | OMe | OMe | 261-264 |
| 1-69 | NHMe | H | N | OMe | OMe | |
| 1-70 | N(Me)2 | H | N | OMe | OMe | |
| 1-71 | NHPh | H | N | OMe | OMe | |
| 1-72 | CO2Et | H | N | OMe | OMe | |
| 1-73 | COMe | H | N | OMe | OMe | |
| 1-74 | Ph | H | N | OMe | OMe | |
| 1-75 | Ph(4-CI) | H | N | OMe | OMe | |
| 1-76 | Ph(4-Me) | H | N | OMe | OMe | |
| 1-77 | Ph(4-OMe) | H · | N | OMe | OMe | |
| 1-78 | CN | H | N | OMe | OMe | |
| 1-79 | no2 | H | N | OMe | OMe | |
| 1-80 | H | 4-Me | CH | OMe | OMe | 138-141 |
| 1-81 | H | 4-C1 | CH | OMe | OMe | |
| 1-82 | H | 5-F | CH | OMe | OMe | 175-178 |
| 1-83 | H | 5-C1 | CH | OMe | OMe | 181-184 |
| 1-84 | H | 5-Br | CH | OMe | OMe | 181-184 |
| 1-85 | H | 5-Me | CH | OMe | OMe | 168-169 |
| 1-86 | H | 5-Bu-t | CH | OMe | OMe | 138-141 |
| 1-87 | H | 5-CF3 | CH | OMe | OMe | 173-174 |
| 1-88 | H | 5-OMe | CH | OMe | OMe | 162-164 |
| 1-89 | H | 5-OEt | CH | OMe | OMe | 169-171 |
| 1-90 | H | 5-OPr | CH | OMe | OMe | |
| 1-91 | H | 5-OCF3 | CH | OMe | OMe | 138-141 |
| 1-92 | H | 5-OCH2CH=CH2 | CH | OMe | OMe | |
| 1-93 | H | 5-OCH2CsCH | CH | OMe | OMe | |
| 1-94 | H | 5-OPh | CH | OMe | OMe | |
| 1-95 | H | 5-OPh(4-Cl) | CH | OMe | OMe | |
| 1-96 | H | 5-OPh(4-Me) | CH | OMe | OMe |
·9·9
ΑΟ (Tabulka 4 )
| 1-------------- sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Ti,20) | |
| 1-97 | H | 5-OPh(4-OMe) | CH | OMe | OMe | ||
| 1-98 | H | 5-SMe | CH | OMe | OMe | ||
| 1-99 | H | 5-CH2OMe | CH | OMe | OMe | ||
| 1-100 | H | 5-COMe | CH | OMe | OMe | ||
| I-1O1 | H | 5-COPh | CH | OMe | OMe | 223-226 | |
| 1-102 | H | 5-CO2Et | CH | OMe | OMe | 185-188 | |
| 1-103 | H | 5-Ph | CH | OMe | OMe | 162-165 | |
| 1-104 | H | 5-Ph(4-Cl) | CH | OMe | OMe | ||
| 1-105 | H | 5-Ph(4-Me) | CH | OMe | OMe | ||
| 1-106 | H | 5-Ph(4-OMe) | CH | OMe | OMe | ||
| 1-107 | H | 5-NO2 | CH | OMe | OMe | ||
| 1-108 | H | 5-NH2 | CH | OMe | OMe | ||
| 1-109 | H | 5-NHMe | CH | OMe | OMe | ||
| 1-110 | H | 5-N(Me)2 | CH | OMe | OMe | ||
| 1-111 | H | 5-CN | CH | OMe | OMe | 249-252 | |
| 1-112 | H | 6-F | CH | OMe | OMe | 192-193 | |
| 1-113 | H | 6-C1 | CH | OMe | OMe | 199-202 | |
| 1-114 | H | 6-Me | CH | OMe | OMe | 134-136 | |
| 1-115 | H | 6-CF3 | CH | OMe | OMe | 192-193 | |
| 1-116 | H | 6-OMe | CH | OMe | OMe | 184-185 | |
| 1-117 | H | 6-CO2Et | CH | OMe | OMe | 184-187 | |
| 1-118 | H | 6-COPh | CH | OMe | OMe | 176-179 | |
| 1-119 | H | 7-Me | CH | OMe | OMe | 134-137 | |
| 1-120 | H | 7-C1 | CH | OMe | OMe | ||
| 1-121 | H | 5,6-Cl2 | CH | OMe | . OMe | 217-220 | |
| 1-122 | H | 5,6-(Me)2 | CH | OMe | OMe | 185-187 | |
| 1-123 | H | 5,6-(OMe)2 | CH | OMe | OMe | ||
| 1-124 | H | 4-Br,6-CF3 | CH | OMe | OMe | 188-191 | |
| 1-125 | H | 4-Cl,6-CF3 | CH | OMe | OMe | 204-206 | |
| 1-126 | H | 4,5,6-F3 | CH | OMe | OMe | ||
| 1-127 | H | 4-Me | N | OMe | OMe | ||
| 1-128 | H | 4-C1 | N | OMe | OMe | ||
| 1-129 | H | 5-F | N | OMe | OMe | ||
| 1-130 | H | 5-C1 | N | OMe | OMe | 175-178 |
AA (Tabulka 5 ) ·♦ · · • · · · ·
9·· · · · * *»· • · · · · · · · · « • ·····♦· 99 99 99 • · · · 9 9 9 99 ♦ · · ♦» · ··99 9
| 1--------------- sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo TÍd20) ' | |
| č. | |||||||
| 1-131 | H | 5-Br | N | OMe | OMe | > 300 | |
| 1-132 | H | 5-1 | N | OMe | OMe | 145-148 | |
| 1-133 | H | 5-Me | N | OMe | OMe | 177-180 | |
| 1-134 | H | 5-Et | N | OMe | OMe | 120-123 | |
| 1-135 | H | 5-Pr | N | OMe | OMe | 101-104 | |
| 1-136 | H | 5-Pr-i | N | OMe | OMe | 87-90 | |
| 1-137 | H | 5-Bu-t | N | OMe | OMe | 146-147 | |
| 1-138 | H | 5-CH=CH2 | N | OMe | OMe | ||
| 1-139 | H | 5-C = CBu | N | OMe | OMe | ||
| 1-140 | H | 5-CF3 | N | OMe | OMe | ||
| 1-141 | H | 5-OMe | N | OMe | OMe | 164-167 | |
| 1-142 | H | 5-OEt | N | OMe | OMe | ||
| 1-143 | H | 5-OPr | N | OMe | OMe | ||
| 1-144 | H | 5-OCF3 | N | OMe | OMe | ||
| 1-145 | H | 5-OCH2CH=CH2 | N | OMe | OMe | ||
| 1-146 | H | 5-OCH2C=CH | N | OMe | OMe | ||
| 1-147 | H | 5-OPh | N | OMe | OMe | ||
| 1-148 | H | 5-OPh(4-Cl) | N | OMe | OMe | ||
| 1-149 | H | 5-OPh(4-Me) | N | OMe | OMe | ||
| 1-150 | H | 5-OPh(4-OMe) | N | . OMe | OMe | ||
| 1-151 | H | 5-SMe | N | OMe | OMe | ||
| 1-152 | H | 5-CH2OMe | N | OMe | OMe | ||
| 1-153 | H | 5-COMe | N | OMe | OMe | ||
| 1-154 | H | 5-COPh | N | OMe | OMe | ||
| 1-155 | H | 5-CO2Et | N | OMe | OMe | ||
| 1-156 | H | 5-Ph | N | OMe | OMe | ||
| 1-157 | H | 5-Ph(4-Cl) | N | OMe | OMe | ||
| 1-158 | H | 5-Ph(4-Me) | N | OMe | OMe | ||
| 1-159 | H | 5-Ph(4-OMe) | N | OMe | OMe | ||
| 1-160 | H | 5-NO2 | N | OMe | OMe | 210-213 | |
| 1-161 | H | 5-NH2 | N | OMe | OMe | ||
| 1-162 | H | 5-NHMe | N | OMe | OMe | ||
| 1-163 | H | 5-N(Me)2 | N | OMe | OMe | ||
| 1-164 | H | 5-CN | N | OMe | OMe |
φ • · · • 4
424 Φ '
Φ· φ
φ φ φ φφφφ •
ΦΦ4Φ «
φ· φ φφφ ( Tabulka 6 )
| 1 sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Tin20) | |
| 1-165 | . Η | 6-F | N | OMe | OMe | ||
| 1-166 | Η | 6-C1 | N | OMe | OMe | ||
| 1-167 | Η | 6-Me | N | OMe | OMe | ||
| 1-168 | Η | 6-CF3 | N | OMe | OMe | ||
| 1-169 | Η | 6-OMe | N | OMe | OMe | ||
| 1-170 | Η | 6-N02 | N | OMe | OMe | >300 | |
| 1-171 | Η | 6-CO2Et | N | OMe | OMe | ||
| 1-172 | Η | 6-COPh | N | OMe | OMe | ||
| 1-173 | Η | 7-Me | N | OMe | OMe | ||
| 1-174 | Η | 7-C1 | N | OMe | OMe | ||
| 1-175 | Η | 5,6-Cl2 | N | OMe | OMe | 176-179 | |
| 1-176 | Η | 5,6-(Me)2 | N | OMe | OMe | 193-196 | |
| 1-177 | Η | 5,6-(OMe)2 | N | OMe | OMe | ||
| 1-178 | Η | 4-Br,6-CF3 | N | OMe | OMe | ||
| 1-179 | Η | 4-Cl,6-CF3 | N | OMe | OMe | ||
| 1-180 | Η | 4,5,6-F3 | N | OMe | OMe | ||
| 1-181 | Me | 4-Me | CH | OMe | OMe | 127-130 | |
| 1-182 | Me | 4-C1 | CH | OMe | OMe | ||
| 1-183 | Me | 5-F | CH | OMe | OMe | 163-165 | |
| 1-184 | Me | . 5-C1 | CH | OMe | OMe | 153-156 | |
| 1-185 | Me | 5-Br | CH | OMe | OMe | 180-183 | |
| 1-186 | Me | 5-Me | CH | OMe | OMe | 163-166 | |
| 1-187 | Me | 5-Bu-t | CH | OMe | OMe | 126-129 | |
| 1-188 | Me | 5-CF3 | CH | OMe | OMe | 129-132 | |
| 1-189 | Me | 5-OMe | CH | OMe | OMe | 190-193 | |
| 1-190 | Me | 5-OEt | CH | OMe | OMe | 211-214 | |
| 1-191 | Me | 5-OPr | CH | OMe | OMe | ||
| 1-192 | Me | 5-OCF3 | CH | OMe | OMe | 137-139 | |
| 1-193 | Me | 5-OPh | CH | OMe | OMe | ||
| 1-194 | Me | 5-CO2Et | CH | OMe | OMe | 173-176 | |
| 1-195 | Me | 5-COPh | CH | OMe | OMe | 169-171 | |
| 1-196 | Me | 5-Ph | CH | OMe | OMe | 164-166 | |
| 1-197 | Me | 5-NH2 | CH | OMe | OMe | ||
| 1-198 | Me | 5-N(Me)2 | CH | OMe | OMe |
(Tabulka 7) sloučenina
| 1-199 | Me | 5-CN | CH | OMe | OMe | 211-214 |
| 1-200 | Me | 6-F | CH | OMe | OMe | 162-163 |
| 1-201 | Me | 6-C1 | CH | OMe | OMe | 165-166 |
| 1-202 | Me | 6-Me | CH | OMe | OMe | 128-131 |
| 1-203 | Me | 6-CF3 | CH | OMe | OMe | 162-165 |
| 1-204 | Me | 6-OMe | CH | OMe | OMe | 158-161 |
| 1-205 | Me | 6-OEt | CH | OMe | OMe | |
| 1-206 | Me | 6-OPr | CH | OMe | OMe | |
| 1-207 | Me | 6-CO2Et | CH | OMe | OMe | 184-187 |
| 1-208 | Me | 6-COPh | CH | OMe | OMe | 179-182 |
| 1-209 | Me | 5,6-Cl2 | CH | OMe | OMe | 204-206 |
| 1-210 | Me | 5,6-(Me)2 | CH | OMe | OMe | 169-172 |
| 1-211 | Me | 5,6-(OMe)2 | CH | OMe | OMe | |
| 1-212 | Me | 4-Me | N | OMe | OMe | 180-182 |
| 1-213 | Me | 4-C1 | N | OMe | OMe | |
| 1-214 | Me | 5-F | N | OMe | OMe | 185-188 |
| 1-215 | Me | 5-C1 | N | OMe | OMe | 173-176 |
| 1-216 | Me | 5-Br | N | OMe | OMe | > 300 |
| 1-217 | Me | 5-1 | N | OMe | OMe | 161-164 |
| 1-218 | Me | 5-Me | N | OMe | OMe | 192-195 |
| 1-219 | Me | 5-Et | N | OMe | OMe | 113-116 |
| 1-220 | Me | 5-Pr | N | OMe | OMe | 128-131 |
| 1-221 | Me | 5-Pr-i | N | OMe | OMe | 124-125 |
| 1-222 | Me | 5-Bu-t | N | OMe | OMe | 143-144 |
| 1-223 | Me | 5-CH=CH2 | N | OMe | OMe | |
| 1-224 | Me | 5-C=CBu | N | OMe | OMe | 111-114 |
| 1-225 | Me | 5-CF3 | N | OMe | OMe | 167-170 |
| 1-226 | Me | 5-OMe | N | OMe | OMe | 161-164 |
| 1-227 | Me | 5-OEt | N | OMe | OMe | |
| 1-228 | Me | 5-OPr | N | OMe | OMe | |
| 1-229 | Me | 5-OCF3 | N | OMe | OMe | 128-131 |
| 1-230 | Me | 5-OPh | N | OMe | OMe | |
| 1-231 | Me | 5-SMe | N | OMe | OMe | |
| 1-232 | Me | 5-CO2Me | N | OMe | OMe | 148-151 |
·· · · (Tabulka 8 ) • · ····
| 1 sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo RI ™ (nD 20) | |
| 1-233 | Me | 5-CO2Et | N | OMe | OMe | ||
| 1-234 | Me | 5-COMe | N | OMe | OMe | 155-158 | |
| 1-235 | Me | 5-COPh | N | OMe | OMe | 163-166 | |
| 1-236 | Me | 5-Ph | N | OMe | OMe | ||
| 1-237 | Me | 5-NH2 | N | OMe | OMe | ||
| 1-238 | Me | 5-N(Me)2 | N | OMe | OMe | ||
| 1-239 | Me | 5-CN | N | OMe | OMe | 188-191 | |
| 1-240 | Me | 6-F | N | OMe | OMe | ||
| 1-241 | Me | 6-C1 | N | OMe | OMe | ||
| 1-242 | Me | 6-Me | N | OMe | OMe | 130-133 | |
| 1-243 | Me | 6-CF3 | N | OMe | OMe | ||
| 1-244 | Me | 6-OMe | N | OMe | OMe | ||
| 1-245 | Me | 6-OEt | N | OMe | OMe | ||
| 1-246 | Me | 6-OPr | N | OMe | OMe | ||
| 1-247 | Me | 6-CO2Et | N | OMe | OMe | ||
| 1-248 | Me | 6-COPh | N | OMe | OMe | ||
| 1-249 | Me | 5,6-Cl2 | N | OMe | OMe | ||
| 1-250 | Me | 4,6-(Me)2 | N | OMe | OMe | 172-175 | |
| 1-251 | Me | 5,6-(Me)2 | N | OMe | OMe | 165-168 | |
| 1-252 | Me | 5,6-(OMe)2 | N | OMe | OMe | ||
| 1-253 | Cl | 4-Me | CH | OMe | OMe | ||
| 1-254 | Cl | 4-Cl | CH | OMe | OMe | ||
| 1-255 | Cl | 5-F | CH | OMe | OMe | 139-142 | |
| 1-256 | Cl | 5-C1 | CH | OMe | OMe | 159-161 | |
| 1-257 | Cl | 5-Br | CH | OMe | OMe | ||
| 1-258 | Cl | 5-Me | CH | OMe | OMe | ' 145-148 | |
| 1-259 | Cl | 5-CF3 | CH | OMe | OMe | 136-139 | |
| 1-260 | Cl | 5-OMe | CH | OMe | OMe | 148-150 | |
| 1-261 | Cl | 5-OEt | CH | OMe | OMe | 187-190 | |
| 1-262 | Cl | 5-OPr | CH | OMe | OMe | ||
| 1-263 | Cl | 5-OCF3 | CH | OMe | OMe | 102-105 | |
| 1-264 | Cl | 5-OPh | CH | OMe | OMe | ||
| [-265 | Cl | 5-COPh | CH | OMe | OMe | ||
| [-266 | Cl | 5-Ph | CH | OMe | OMe 1 |
(Tabulka 9 ) sloučenina ··♦·
| č. | X | Yn | A | R1 | R2 | nebo |
| 1-26' | Cl | 5-NH2 | CH | OMe | OMe | |
| I-26Í | Cl | 5-N(Me)2 | CH | OMe | OMe | |
| I-26S | Cl | 5-CN | CH | OMe | OMe | |
| 1-270 | Cl | 6-F | CH | OMe | OMe | |
| 1-271 | Cl | 6-Cl | CH | OMe | OMe | 163-164 |
| 1-272 | Cl | 6-Me | CH | OMe | OMe | 98-101 |
| 1-273 | Cl | 5,6-(OMe)2 | CH | OMe | OMe | |
| 1-274 | Cl | 4-Me | N | OMe | OMe | |
| 1-275 | Cl | 4-C1 | N | OMe | OMe | |
| 1-276 | Cl | 5-F | N | OMe | OMe | |
| 1-277 | Cl | 5-C1 | N | OMe | OMe | 146-149 |
| 1-278 | Cl | 5-Br | N | OMe | OMe | |
| 1-279 | Cl | 5-Me | N | OMe | OMe | 159-162 |
| 1-280 | Cl | 5-CF3 | N | OMe | OMe | |
| 1-281 | Cl | 5-OMe | N | OMe | OMe | |
| 1-282 | Cl | 5-OEt | N | OMe | OMe | |
| 1-283 | Cl | 5-OPr | N | OMe | OMe | |
| 1-284 | Cl | 5-OCF3 | N | OMe | OMe | |
| 1-285 | Cl | 5-OPh | N | OMe | OMe | |
| 1-286 | Cl | 5-COPh | N | OMe | OMe | |
| 1-287 | Cl | 5-Ph | N | OMe | OMe | |
| 1-288 | Cl | 5-NH2 | N | OMe | OMe | |
| 1-289 | Cl | 5-N(Me)2 | N | OMe | OMe | |
| 1-290 | Cl | 5-CN | N | OMe | OMe | |
| 1-291 | Cl | 6-F | N | OMe | OMe | |
| 1-292 | Cl | 6-C1 | N | OMe | OMe | |
| 1-293 | Cl | 6-Me | N | OMe | OMe | |
| 1-294 | Cl | 5,6-(OMe)2 | N | OMe | OMe | |
| 1-295 | cf3 | 5-F | CH | OMe | OMe | 133-136 |
| 1-296 | cf3 | 5-C1 | CH | OMe | OMe | 114-116 |
| 1-297 | cf3 | 5-Br | CH | OMe | OMe | |
| 1-298 | cf3 | 5-Me | CH | OMe | OMe | 93-96 |
| 1-299 | cf3 | 5-CF3 | CH | OMe | OMe | 78-79 |
| 1-300 | cf3 | 5-OMe | CH | OMe | OMe | 129-132 |
• · ··<· ( Tabulka 10)
| 1--------------- sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo *nD 20) | |
| v c. | |||||||
| 1-301 | cf3 | 5-OEt | CH | OMe | OMe | 151-154 | |
| 1-302 | cf3 | 5-OPr | CH | OMe | OMe | ||
| 1-303 | cf3 | 5-N(Me)2 | CH | OMe | OMe | ||
| 1-304 | cf3 | 5-CN | CH | OMe | OMe | ||
| 1-305 | cf3 | 6-F | CH | OMe | OMe | ||
| 1-306 | cf3 | 6-C1 | CH | OMe | OMe | ||
| 1-307 | cf3 | 6-Me | CH | OMe | OMe | 132-135 | |
| 1-308 | cf3 | 5,6-(OMe)2 | CH | OMe | OMe | ||
| 1-309 | cf3 | 5-F | N | OMe | OMe | 170-173 | |
| 1-310 | cf3 | 5-C1 | N | OMe | OMe | 135-138 | |
| 1-311 | cf3 | 5-Br | N | OMe | OMe | 111-114 | |
| 1-312 | cf3 | 5-Me | N | OMe | OMe | 137-140 | |
| 1-313 | cf3 | 5-Et | N | OMe | OMe | 104-107 | |
| 1-314 | cf3 | 5-Pr | N | OMe | OMe | 89-92 | |
| 1-315 | cf3 | 5-Pr-i | N | OMe | OMe | 118-121 | |
| 1-316 | cf3 | 5-Bu-t | N | OMe | OMe | . 113-116 | |
| 1-317 | cf3 | 5-CF3 | N | OMe | OMe | ||
| 1-318 | cf3 | 5-OMe | N | OMe | OMe | 165-168 | |
| 1-319 | cf3 | 5-OEt | N | OMe | OMe | ||
| I-32Q | cf3 | 5-OPr | N | OMe | OMe | ||
| 1-321 | cf3 | 5-OCFa | N | OMe | OMe. | 187-190 | |
| 1-322 | cf3 | 5-SMe | N | OMe | OMe | ||
| 1-323 | cf3 | 5-NHMe | N | OMe | OMe | ||
| 1-324 | cf3 | 5-N(Me)2 | N | OMe | OMe | ||
| 1-325 | cf3 | 5-CN | N | OMe | OMe | 188-191 | |
| 1-326 | cf3 | 5-CO2Me | N | OMe | OMe | 126-129 | |
| 1-327 | cf3 · | 5-1 | N | OMe | OMe | 115-118 | |
| 1-328 | cf3 | 6-F | N | OMe | OMe | ||
| 1-329 | cf3 | 6-C1 | N | OMe | OMe | ||
| 1-330 | cf3 | 6-Me | N | OMe | OMe | ||
| 1-331 | cf3 | 5,6-(OMe)2 | N | OMe | OMe | ||
| 1-332 | Et | 5-F | CH | OMe | OMe | 135-138 | |
| 1-333 | Et | 5-C1 | CH | OMe | OMe | 137-140 | |
| 1-334 | Et | 5-Me | CH | OMe | OMe | 120-122 |
(Tabulka 11 )
| 1 sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo Tnn 20) | |
| u. | |||||||
| 1-335 | Et | 5-CF3 | CH | OMe | OMe | 117-118 | |
| 1-336 | Et | 5-OMe | CH | OMe | OMe | 118-120 | |
| 1-337 | Et | 5-OEt | CH | OMe | OMe | ||
| 1-338 | Et | 5-OPr | CH | OMe | OMe | ||
| 1-339 | Et | 5-N(Me)2 | CH | OMe | OMe | ||
| 1-340 | Et | 5-CN | CH | OMe | OMe | ||
| 1-341 | Et | 6-F | CH | OMe | OMe | ||
| 1-342 | Et | 6-C1 | CH | OMe | OMe | ||
| 1-343 | Et | 6-Me | CH | OMe | OMe | ||
| 1-344 | Et | 5,6-(OMe)2 | CH | OMe | OMe | ||
| 1-345 | Et | 5-F | N | OMe | OMe | ||
| 1-346 | Et | 5-C1 | N | OMe | OMe | 125-128 | |
| 1-347 | Et | 5-Me | N | OMe | OMe | ||
| 1-348 | Et | 5-CF3 | N | OMe | OMe | ||
| 1-349 | Et | 5-OMe | N | OMe | OMe | ||
| 1-350 | Et | 5-OEt | N | OMe | OMe | ||
| 1-351 | Et | 5-OPr | N | OMe | OMe | ||
| 1-352 | Et | 5-N(Me)2 | N | OMe | OMe | ||
| 1-353 | Et | 5-CN | N | OMe | OMe | ||
| 1-354 | Et | 6-F | N | OMe | OMe | ||
| 1-355 | Et | 6-Cl | N | OMe | OMe | ||
| 1-356 | Et | 6-Me | N | OMe | OMe | ||
| 1-357 | Et | 5,6-(OMe)2 | N | OMe | OMe | ||
| 1-358 | Pr | 5-C1 | N | OMe | OMe | 128-131 | |
| 1-359 | Pr-i | 5-C1 | N | OMe | OMe | 160-163 | |
| 1-360 | Pr-c | 5-C1 | N | OMe | OMe | 146-149 | |
| 1-361 | nh2 | 5-F | CH | OMe | OMe | 236-239 | |
| 1-362 | nh2 | 5-Me | CH | OMe | OMé | >300 | |
| 1-363 | nh2 | 5-CF3 | CH | OMe | OMe | 268-271 | |
| 1-364 | nh2 | 5-OMe | CH | OMe | OMe | 232-235 | |
| 1-365 | nh2 | 5-OEt | CH | OMe | OMe | 239-242 | |
| 1-366 | nh2 | 6-Me | CH | OMe | OMe | >300 | |
| 1-367 | nh2 | 5,6-(OMe)2 | CH | OMe | OMe | ||
| [-368 | nh2 | 5-C1 | N | OMe | OMe | 293-296 |
>· «··· (Tabulka 12 )
| í-------------- sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo ωο20) | |
| v c. | |||||||
| 1-369 | nh2 | 5-Me | N | OMe | OMe | 272-275 | |
| 1-370 | nh2 | 5-CF3 | N | OMe | OMe | ||
| 1-371 | nh2 | 5-OMe | N | OMe | OMe | ||
| 1-372 | nh2 | 5-OEt | N | OMe | OMe | ||
| 1-373 | NH, | 6-Me | N | OMe | OMe | ||
| 1-374 | nh2 | 5,6-(OMe)2 | N | OMe | OMe | ||
| 1-375 | NHMe | 5-C1 | N | OMe | OMe | 238-241 | |
| 1-376 | N(Me)2 | 5-C1 | N | OMe | OMe | 66-69 | |
| 1-377 | CH2OMe | 5-C1 | N | OMe | OMe | 105-108 | |
| 1-378 | Ph | 5-C1 | N | OMe | OMe | 137-140 | |
| 1-379 | Bn | 5-C1 | N | OMe | OMe | 192-195 | |
| 1-380 | CN | 5-C1 | CH | OMe | OMe | 223-226 | |
| 1-381 | CN | 5-Me | CH | OMe | OMe | 229-231 | |
| 1-382 | CN | 5-CF3 | CH | OMe | OMe | ||
| 1-383 | CN | 5-OMe | CH | OMe | OMe | ||
| 1-384 | CN | 5-C1 | N | OMe | OMe | ||
| 1-385 | CN | 5-Me | N | OMe | OMe | ||
| 1-386 | CN | 5-CF3 | N | OMe | OMe | ||
| 1-387 | CN | 5-OMe | N | OMe | OMe | ||
| 1-388 | SMe | 5-C1 | CH | OMe | OMe | 184-187 | |
| 1-389 | SMe | 5-Me | CH | OMe | OMe | 155-158 | |
| 1-390 | SMe | 5-CF3 | CH | OMe | OMe | ||
| 1-391 | SMe | 5-OMe | CH | OMe | OMe | ||
| 1-392 | SMe | 6-C1 | CH | OMe | OMe | ||
| 1-393 | SMe | 6-Me | CH | OMe | OMe | ||
| 1-394 | SMe | 5-Cl | N | OMe | OMe | 135-138 | |
| 1-395 | SMe | 5-Me | N | OMe | OMe | ||
| 1-396 | SMe | 5-CF3 | N | OMe | OMe | ||
| 1-397 | SMe | 5-OMe | N | OMe | OMe | ||
| 1-398 | SMe | 6-C1 | N | OMe | OMe | ||
| 1-399 | SMe | 6-Me | N | OMe | OMe | ||
| 1-400 | CC13 | 5-C1 | CH | OMe | OMe | 132-134 | |
| 1-401 | CC13 | 5-Me | CH | OMe | OMe | ||
| 1-402 | CC13 | 5-OMe | CH | OMe | OMe |
·· ·· 0 « (Tabulka 13 ) í<?
| 1------------------ sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ^°) | |
| 1-403 | CC13 | 6-C1 | CH | OMe | OMe | ||
| 1-404 | CC13 | 6-Me | CH | OMe | OMe | 136-139 | |
| 1-405 | CC13 | 5-C1 | N | OMe | OMe | 123-126 | |
| 1-406 | CC13 | 5-Me | N | OMe | OMe | 140-151 | |
| 1-407 | CC13 | 5-OMe | N | OMe | OMe | ||
| 1-408 | CC13 | 5-Br | N | OMe | OMe | ||
| 1-409 | CC13 | 6-C1 | N | OMe | OMe | ||
| 1-410 | CC13 | 6-Me | N | OMe | OMe | ||
| 1-411 | CF2C1 | 5-Me | N | OMe | OMe | 109-111 | |
| 1-412 | cf2ci | 5-C1 | N | OMe | OMe | 86-89 | |
| 1-413 | cf2ci | 5-Bi' | N | OMe | OMe | ||
| 1-414 | cf2ci | 5-OMe | N | OMe | OMe | ||
| 1-415 | ch2ci | 5-Me | N | OMe | OMe | 143-145 | |
| 1-416 | ch2ci | 5-C1 | N | OMe | OMe | 160-161 | |
| 1-417 | ch2ci | 5-Br | N | OMe | OMe | ||
| 1-418 | ch2ci | 5-OMe | N | OMe | OMe | ||
| 1-419 | c2f5 | 5-Me | N | OMe | OMe | ||
| 1-420 | C2F5 | 5-C1 | N | OMe | OMe | ||
| 1-421 | C2FS | 5-Br | N | OMe | OMe | ||
| 1-422 | c2f5 | 5-OMe | N | OMe | OMe | ||
| 1-423 | SO2Me | 5-C1 | CH | OMe | OMe | 149-152 | |
| 1-424 | SO2Me | 5-Me | CH | OMe | OMe | 176-177 | |
| 1-425 | SO2Me | 6-Me | CH | OMe | OMe | ||
| 1-426 | SO2Me | 5-C1 | N | OMe | OMe | ||
| 1-427 | SO2Me | 5-Me | N | OMe | OMe | ||
| 1-428 | SO2Me | 6-Me | N | OMe | OMe | ||
| 1-429 | OMe | 5-C1 | CH | OMe | OMe | 182-185 | |
| 1-430 | OMe | 6-C1 | CH | OMe | OMe | 178-180 | |
| 1-431 | OMe | 5-C1 | N | OMe | OMe | ||
| 1-432 | OMe | 6-C1 | N | OMe | OMe | ||
| 1-433 | H | H | N | OMe | OEt | ||
| 1-434 | H | 5-C1 | N | OMe | OEt | ||
| 1-435 | H | 5-Br | N | OMe | OEt | 194-196 | |
| 1-436 | H | 5-Me | N | OMe | OEt | 1 |
Φ··Φ
·· (Tabulka 14 )
| 1-------------- sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo Ti20) | |
| c. | |||||||
| 1-437 | Me | H | N | OMe | OEt | ||
| 1-438 | Me | 5-C1 | N | OMe | OEt | 153-156 | |
| 1-439 | Me | 5-Br | N | OMe | OEt | 143-145 | |
| 1-440 | Me | 5-Me | N | OMe | OEt | 155-156 | |
| 1-441 | Cl | 5-C1 | N | OMe | OEt | ||
| 1-442 | Cl | 5-Br | N | OMe | OEt | ||
| 1-443 | Cl | 5-Me | N | OMe | OEt | ||
| 1-444 | cf3 | H | N | OMe | OEt | ||
| 1-445 | cf3 | 5-Me | N | OMe | OEt | 147-150 | |
| 1-446 | cf3 | 5-C1 | N . | OMe | OEt | 149-151 | |
| 1-447 | cf3 | 5-Br | N | OMe | OEt | 138-139 | |
| 1-448 | cf2ci | 5-C1 | N | OMe | OEt | ||
| 1-449 | cf2ci | 5-Br | N | OMe | OEt | ||
| 1-450 | cf2ci | 5-Me | N | OMe | OEt | ||
| 1-451 | ch2ci | 5-C1 | N | OMe | OEt | ||
| 1-452 | ch2ci | 5-Br | N | OMe | OEt | ||
| 1-453 | ch2ci | 5-Me | N | OMe | OEt | ||
| 1-454 | c2f5 | 5-C1 | N | OMe | OEt | ||
| 1-455 | c2f6 | 5-Br | N | OMe | OEt | ||
| 1-456 | C2Fs | 5-Me | N | OMe | OEt | ||
| 1-457 | H | H | CH | OEt | OEt | 122-124 | |
| 1-458 | Cl | H | CH | OEt | OEt | 79-82 | |
| 1-459 | Br | H | CH | OEt | OEt | ||
| 1-460 | SMe | H | CH | OEt | OEt | 122-125 | |
| 1-461 | Me | H | CH | OEt | OEt | 88-91 | |
| 1-462 | Et | H | CH | OEt | OEt | 90-93 | |
| 1-463 | OMe | H | CH | OEt | OEt | 87-89 | |
| 1-464 | OEt | H | CH | OEt | OEt | 96-99 | |
| 1-465 | cf3 | H | CH | OEt | OEt | 90-92 | |
| 1-466 | nh2 | H | CH | OEt | OEt | 222-225 | |
| 1-467 | CN | H | CH | OEt | OEt | 153-156 | |
| 1-468 | H | H | N | OEt | OEt | ||
| 1-469 | Cl | H | N | OEt | OEt | ||
| [-470 | Br | H | N | OEt | OEt |
(Tabulka 15 )
| ·· | • | ·· ···· | • 4 | * | ||
| • | • | • | • » · | 4 | • | ·· |
| • · | • · | • · · | • | • | • | |
| • | • | • ♦·· | • · · · | • ♦ | • | • |
| • | • | • | • · · | • | • | • |
| «· | • | ·· · | ·· | ··· |
| (--------------- sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo úl20) | |
| 1-471 | SMe | H | N | OEt | OEt | ||
| 1-472 | Me | H | N | OEt | OEt | ||
| 1-473 | Et | H | N | OEt | OEt | ||
| 1-474 | OMe | H | N | OEt | OEt | ||
| 1-475 | OEt | H | N | OEt | OEt | ||
| 1-476 | cf3 | H | N | OEt | OEt | ||
| 1-477 | nh2 | H | N | OEt | OEt | ||
| 1-478 | CN | H | N | OEt | OEt | ||
| 1-479 | H | 5-F | CH | OEt . | OEt | 156-159 | |
| 1-480 | H | 5-C1 | CH | OEt | OEt | 177-180 | |
| 1-481 | H | 5-Br | CH | OEt | OEt | ||
| 1-482 | H | 5-Me | CH | OEt | OEt | 135-138 | |
| 1-483 | H | 5-CF3 | CH | OEt | OEt | 165-168 | |
| 1-484 | H | 5-OMe | CH | OEt | OEt | ||
| 1-485 | H | 5-OEt | CH | OEt | OEt | ||
| 1-486 | H | 6-C1 | CH | OEt | OEt | 164-167 | |
| 1-487 | H | 5,6-(OMe)2 | CH | OEt | OEt | ||
| 1-488 | H | 5-F | N | OEt | OEt | ||
| 1-489 | H | 5-C1 | N | OEt | OEt | ||
| 1-490 | H | 5-Br | N | OEt | OEt | 170-173 | |
| 1-491 | H | 5-Me | N | OEt | OEt | ||
| 1-492 | H | 5-Bu-t | N | OEt | OEt | 107-110 | |
| 1-493 | H | 5-CF3 | N | OEt | OEt | ||
| 1-494 | H | 5-OMe | N | OEt | OEt | ||
| 1-495 | H | 5-OEt | N | OEt | OEt | ||
| 1-496 | H | 6-C1 | N | OEt | OEt | ||
| 1-497 | H | 5,6-(OMe)2 | N | OEt | OEt | ||
| 1-498 | Me | 5-F | CH | OEt | OEt | 131-133 | |
| 1-499 | Me | 5-C1 | CH | OEt | OEt | 171-174 | |
| 1-500 | Me | 5-Br | CH | OEt | OEt | ||
| 1-501 | Me | 5-Me | CH | OEt | OEt | 119-122 | |
| 1-502 | Me | 5-CF3 | CH | OEt | OEt | 131-134 | |
| 1-503 | Me | 5-OMe | CH | OEt | OEt | 141-144 | |
| 1-504 | Me | 5-OEt | CH | OEt | OEt |
• · (Tabulka 16 )
| 1 sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo | |
| č. | |||||||
| 1-505 | Me | 5-OCF3 | CH | OEt | OEt | ||
| 1-506 | Me | 5-CN | CH | OEt | OEt | ||
| 1-507 | Me | 6-F | CH | OEt | OEt | 133-134 | |
| 1-508 | Me | 6-Cl | CH | OEt | OEt | 146-149 | |
| 1-509 | Me | 6-Me | CH | OEt | OEt | ||
| 1-510 | Me | 6-CF3 | CH | OEt | OEt | 138-141 | |
| 1-511 | Me | 6-OMe | CH | OEt | OEt | 135-138 | |
| 1-512 | Me | 5,6-(OMe)2 | CH | OEt | OEt | ||
| 1-513 | Me | 5-F | N | OEt | OEt | ||
| 1-514 | Me | 5-C1 | N | OEt | OEt | 175-178 | |
| 1-515 | Me | 5-Br | N | OEt | OEt | 169-172 | |
| 1-516 | Me | 5-Me | N | OEt | OEt | 141-144 | |
| 1-517 | Me | 5-Bu-t | N | OEt | OEt | 107-109 | |
| 1-518 | Me | 5-CF3 | N | OEt | OEt | ||
| 1-519 | Me | 5-OMe | N | OEt | OEt | ||
| 1-520 | Me | 5-OEt | N | OEt | OEt | ||
| 1-521 | Me | 5-OCFa | N | OEt | OEt | ||
| 1-522 | Me | 5-CN | N | OEt | OEt | ||
| 1-523 | Me | 6-F | N | OEt | OEt | ||
| 1-524 | Me | 6-C1 | N | OEt | OEt | ||
| 1-525 | Me | 6-Me | N | OEt | OEt | ||
| 1-526 | Me | 6-CF3 | N | OEt | OEt | ||
| 1-527 | Me | 6-OMe | N | OEt | OEt | ||
| 1-528 | Me | 5,6-(OMe)2 | N | OEt | OEt | ||
| 1-529 | Cl | 5-C1 | CH | OEt | OEt | ||
| 1-530 | Cl | 5-Me | CH | OEt · | OEt | 101-103 | |
| 1-531 | Cl | 5-OMe | CH | OEt | OEt | 153-156 | |
| 1-532 | Cl | 5-OEt | CH | OEt | OEt | ||
| 1-533 | Cl | 5,6-(OMe)2 | CH | OEt | OEt | ||
| 1-534 | Cl | 5-C1 | N | OEt | OEt | 130-133 | |
| 1-535 | Cl | 5-Me | N | OEt | OEt | ||
| 1-536 | Cl | 5-OMe | N | OEt | OEt | ||
| 1-537 | Cl | 5-OEt | N | OEt | OEt | ||
| 1-538 | Cl | 5,6-(OMe)2 | N | OEt | OEt |
·· · ·
2S (Tabulka 17) (nD 20)
| 1-539 | cf3 | 5-Me | CH | OEt | OEt | |
| 1-540 | cf3 | 5-OMe | CH | OEt | OEt | |
| 1-541 | cf3 | 5,6-(OMe)2 | CH | OEt | OEt | |
| 1-542 | cf3 | H | N | OEt | OEt | |
| 1-543 | cf3 | 5-Me | N | OEt | OEt | 163-165 |
| 1-544 | cf3 | 5-OMe | N | OEt | OEt | 140-143 |
| 1-545 | cf3 | 5-C1 | N | OEt | OEt | 138-141 |
| 1-546 | cf3 | 5-Br | N | OEt | OEt | 120-123 |
| 1-547 | Et | 5-Me | CH | OEt | OEt | |
| 1-548 | Et | 5-OMe | CH | OEt | OEt | |
| 1-549 | Et | 5,6-(OMe)2 | CH | OEt | OEt | |
| 1-550 | CC13 | 5-C1 | N | OEt | OEt | 110-113 |
| 1-551 | CC13 | 5-Br | N | OEt | OEt | |
| 1-552 | CC13 | 5-Me | N | OEt | OEt | |
| 1-553 | CC13 | 5-OMe | N | OEt | OEt | |
| 1-554 | CF2C1 | 5-C1 | N | OEt | OEt | |
| 1-555 | cf2ci | 5-Br | N | OEt | OEt | |
| 1-556 | cf2ci | 5-Me | N | OEt | OEt | |
| 1-557 | ch2ci | 5-C1 | N | OEt | OEt | |
| 1-558 | ch2ci | 5-Br | N | OEt | OEt | |
| 1-559 | ch2ci . | 5-Me | N | OEt | OEt | |
| 1-560 | c2F5 | 5-C1 | N | OEt | OEt | |
| 1-561 | c2f5 | 5-Br | N | OEt | OEt | |
| 1-562 | c2f6 | 5-Me | N | OEt | OEt | |
| 1-563 | CN | 5-C1 | CH | OEt | OEt | 170-172 |
| 1-564 | CN | 5-OMe | CH | OEt | OEt | |
| 1-565 | CN | 5,6-(OMe)2 | CH | OEt | OEt | |
| 1-566 | CN | 5-Me | N | OEt | OEt | |
| 1-567 | CN | 5-OMe | N | OEt | OEt | |
| 1-568 | CN | 5-C1 | N | OEt | OEt | |
| 1-569 | SMe | 5-C1 | CH | OEt | OEt | 167-169 |
| 1-570 | SMe | 5-Me | CH | OEt | OEt | |
| 1-571 | SMe | 5-C1 | N | OEt | OEt | |
| 1-572 | SMe | 5-Me | N | OEt | OEt |
« ·
ZQ·· ·· · · (Tabulka 18)
| p— sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo | |
| 1-573 | SO2Me | 5-C1 | CH | OEt | OEt | 167-170 | |
| 1-574 | SO2Me | 5-Me | CH | OEt | OEt | ||
| 1-575 | OMe | 5-Cl | CH | OEt | OEt | 143-146 | |
| 1-576 | H | H | CH | OPr | OPr | 89-90 | |
| 1-577 | H | H | N | OPr | OPr | ||
| 1-578 | H | 5-C1 | N | OPr | OPr | ||
| 1-579 | H | 5-Br | N | OPr | OPr | ||
| 1-580 | Me | 5-C1 | N | OPr | OPr | 128-131 | |
| 1-581 | Me | 5-Br | N | OPr | OPr | ||
| 1-582 | Me | 5-Me | N | OPr | OPr | ||
| 1-583 | cf3 | 5-C1 | N | OPr | OPr | 71-74 | |
| 1-584 | cf3 | 5-Br | N. | OPr | OPr | ||
| 1-585 | cf3 | 5-Me | N | OPr | OPr | ||
| 1-586 | H | H | CH | OPr-i | OPr-i | 115-117 | |
| 1-587 | Me | 5-C1 | CH | OPr-i | OPr-i | ||
| 1-588 | Me | 5-Me | CH | OPr-i | OPr-i | ||
| 1-589 | H | H | N | OPr-i | OPr-i | ||
| 1-590 | H | 5-C1 | N | OPr-i | OPr-i | ||
| 1-591 | H | 5-Br | N | OPr-i | OPr-i | ||
| 1-592 | Me | 5-C1 | N | OPr-i | OPr-i | 85-88 | |
| 1-593 | Me | 5-Br | N | OPr-i | OPr-i | ||
| 1-594 | Me | 5-Me | N | OPr-i | OPr-i | ||
| 1-595 | cf3 | 5-C1 | N | OPr-i | OPr-i | 97-100 | |
| 1-596 | cf3 | 5-Br | N | OPr-i | OPr-i | ||
| 1-597 | cf3 | 5-Me | N | OPr-i | OPr-i | ||
| 1-598 | H | H | N | OCH2CH=CH2 | och2ch=ch2 | ||
| 1-599 | H | 5-C1 | N | OCH2CH=CH2 | och2ch=ch2 | ||
| 1-600 | H | 5-Br | N | och2ch=ch2 | och2ch=ch2 | ||
| 1-601 | Me | 5-C1 | N | och2ch=ch2 | och2ch=ch2 | 158-161 | |
| 1-602 | Me | 5-Br | N | och2ch=ch2 | och2ch=ch2 | ||
| 1-603 | Me | 5-Me | N | och2ch=ch2 | och2ch=ch2 | ||
| 1-604 | cf3 | 5-C1 | N | och2ch=ch2 | och2ch=ch2 | ||
| 1-605 | cf3 | 5-Br | N | och2ch=ch2 | och2ch=ch2 | ||
| 1-606 | cf3 | 5-Me | N | och2ch=ch2 | och2ch=ch2 |
• ·
( Tabulka 19 )
| íenina č. | X | Yn | A |
| 1-607 | H | H | N |
| 1-608 | H | 5-C1 | N |
| 1-609 | H | 5-Br | N |
| 1-610 | Me | 5-C1 | N |
| 1-611 | Me | 5-Br | N |
| 1-612 | Me | 5-Me | N |
| 1-613 | cf3 | 5-C1 | N |
| 1-614 | cf3 | 5-Br | N |
| 1-615 | cf3 | 5-Me | N |
| 1-616 | Me | 5-C1 | CH |
| 1-617 | Me | 5-Me | CH |
| 1-618 | H | 5-Br | N |
| 1-619 | Me | 5-C1 | N |
| 1-620 | Me | 5-Br | N |
| 1-621 | Me | 5-Me | N |
| 1-622 | cf3 | 5-C1 | N |
| 1-623 | cf3 | 5-Br | N |
| 1-624 | cf3 | 5-Me | N |
| 1-625 | Me | 5-Cl | CH |
| 1-626 | Me | 5-Me | CH |
| 1-627 | H | 5-Br | N |
| 1-628 | Me | 5-C1 | N |
| 1-629 | Me | 5-Br | N |
| 1-630 | Me | 5-Me | N |
| 1-631 | cf3 | 5-C1 | N |
| 1-632 | cf3 | 5-Br | N |
| 1-633 | cf3 | 5-Me | N |
| 1-634 | H | 5-Br | N |
| 1-635 | Me | 5-C1 | N |
| 1-636 | Me | 5-Br | N |
| 1-637 | Me | 5-Me | N |
| 1-638 | cf3 | 5-Cl | N |
| 1-639 | cf3 | 5-Br | N |
| 1-640 | cf3 | 5-Me | N |
| R1 | R2 | m.p. (°C) nebo ^») |
| OCH2C=CH | OCH2C = CH | |
| och2c^ch | och2c^ch | |
| OCH2C=CH | och2c^ch | |
| OCH2C=CH | OCH2CsCH | |
| 0 CIRCÍCH | och2c=ch | |
| OCH2C=CH | OCH2CsCH | |
| 0 CIRCÍCH | och2c=ch | |
| OCH2CsCH | OCH2CsCH | |
| och2c^ch | OCH2CsCH | |
| och2cn | OCH2CN | |
| och2cn | OCH2CN | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| och2cn | och2cn | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2CH2OMe | OCH2CH2OMe | |
| OCH2Pr-c | OCH2Pr-c | |
| OCH2Pr-c | OCH2Pr-c | |
| OCH2Pr-c | OCH2Pr-c | |
| OCH2Pr-c | OCH2Pr-c | |
| OCH2Pr-c | 0CH2Pr-c | |
| OCH2Pr-c | OCH2Pr-c | |
| OCH2Pr-c | OCH2Pr-c |
• · • · · • · · · • · · · · • · · <» O
I sloučenina (Tabulka 20 )
m.p. (°C) nebo
| 1-641 | Me | 5-Me | CH | OCH2CH2C1 | OCH2CH2Cl | |
| 1-642 | Me | 5-C1 | CH | OCH2CH2C1 | och2ch2ci | |
| 1-643 | Me | 5-Me | N | OCH2CH2C1 | och2ch2ci | |
| 1-644 | Me | 5-C1 | N | OCH2CH2C1 | och2ch2ci | |
| 1-645 | cf3. | 5-Me | N | och2ch2ci | och2ch2ci | |
| 1-646 | cf3 | 5-Cl | N | och2ch2ci | och2ch2ci | |
| 1-647 | Me | 5-C1 | N | och2ch2f | och2ch2f | |
| 1-648 | Me | 5-Me | N | och,ch2f | och2ch2f | |
| 1-649 | cf3 | 5-Me | N | och2ch2f | och2ch2f | |
| 1-650 | cf3 | 5-C1 | N | och2ch2f | och2ch2f | |
| 1-651 | Me | 5-C1 | N | och2cf3 | och2cf3 | |
| 1-652 | Me | .5-Me | N | och2cf3 | och2cf3 | |
| 1-653 | cf3 | 5-Me | N | och2cf3 | OCH2CF3 | |
| 1-654 | cf3 | 5-C1 | N | och2cf3 | OCH2CF3 | |
| 1-655 | H | H | CH | OBn | OBn | |
| 1-656 | H | H | N | OBn | OBn | |
| 1-657 | H | H | N | OBn(4-Cl) | 0Bn(4-Cl) | |
| 1-658 | H | H | N | OBn(4-Me) | OBn(4-Me) | |
| 1-659 | H | H | N | OBn(4-OMe) | OBn(4-OMe) | |
| 1-660 | H | H | CH | OMe * | OPh | 131-132 |
| 1-661 | H | H | N | OMe | OPh | |
| 1-662 | H | H | N | OMe | OPh(4-Cl) | |
| 1-663 | H | H | N | OMe | OPh(4-Me) | |
| 1-664 | H | H | N | OMe | OPh(4-OMe) | |
| 1-665 | H | H | CH | OMe | OCHF2 | 138-139 |
| 1-666 | H | H | N | OMe | ochf2 | |
| 1-667 | H | H | CH | OMe | H | 114-116 |
| 1-668 | Me | H | CH | OMe | H | |
| 1-669 | H | 5-C1 | CH | OMe | H | 173-176 |
| 1-670 | H | 5-Me | CH | OMe | H | 140-142 |
| 1-671 | Me | 5-C1 | CH | OMe | H | 127-130 |
| 1-672 | Me | 5-Me | CH | OMe | H | 113-114 |
| 1-673 | Me | 5-CF3 | CH | OMe | H | |
| 1-674 | Me | 5-OMe | CH | OMe | H |
27(Tabulka 21 )
| 1 sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Sd20) | |
| 1-675 | Me | 6-C1 | CH | OMe | H | 126-130 | |
| 1-676 | Me | 5,6-(OMe)2 | CH | OMe | H | ||
| 1-677 | Cl | . 5-C1 | CH | OMe | H | ||
| 1-678 | Cl | 5-Me | CH | OMe | H | ||
| 1-679 | Cl | 5-CF3 | CH | OMe | H | ||
| 1-680 | Cl | 5-OMe | CH | OMe | H | ||
| 1-681 | Cl | 5,6-(OMe)2 | CH | OMe | H | ||
| 1-682 | cf3 | 5-C1 | CH | OMe | H | 107-108 | |
| 1-683 | cf3 | 5-Me | CH | OMe | H | 76-79 | |
| 1-684 | cf3 | 5-CF3 | CH | OMe | H | ||
| 1-685 | cf3 | 5-OMe | CH | OMe | H | ||
| 1-686 | Et | 5-C1 | CH | OMe | H | ||
| 1-687 | Et | 5-Me | CH | OMe | H | ||
| 1-688 | Et | 5-CF3 | CH | OMe | H | ||
| 1-689 | Et | 5-OMe | CH | OMe | H | ||
| 1-690 | H | H | CH | OEt | H | 104-107 | |
| 1-691 | Me | H | CH | OEt | H | ||
| 1-692 | H | 5-C1 | CH | OEt | H | 158-160 | |
| 1-693 | H | 5-Me | CH | OEt | H | 131-132 | |
| 1-694 | Me | 5-Cb | CH | OEt | H | 153-155 | |
| 1-695 | Me | 5-Me | CH | OEt | H | 109-111 | |
| 1-696 | Me | 5-CF3 | CH | OEt | H | ||
| 1-697 | Me | 5-OMe | CH | OEt | H | ||
| 1-698 | Me | 5,6-(OMe)2 | CH | OEt | H | ||
| 1-699 | Me | 6-C1 | CH | OEt | H | 117-118 | |
| 1-700 | Cl | 5-Me | CH | OEt | H | ||
| 1-701 | Cl | 5-CF3 | CH | OEt | H | ||
| 1-702 | Cl | 5-OMe | CH | OEt | H | ||
| 1-703 | Cl | 5,6-(OMe)2 | CH | OEt | H | ||
| 1-704 | cf3 | 5-C1 | CH | OEt | H | 125-128 | |
| 1-705 | cf3 | 5-Me | CH | OEt | H | 86-87 | |
| 1-706 | cf3 | 5-OMe | CH | OEt | H | ||
| [-707 | Et | 5-C1 | CH | OEt | H | ||
| 1-708 | Et | 5-Me | CH | OEt | H |
• ·
(Tabulka 22 ) (np20)
| 1-709 | Et | 5-CF3 | CH | OEt | Η | |
| 1-710 | Et | 5-OMe | CH | OEt | H | |
| 1-711 | H | H | CH | OPr | H | 83-86 |
| 1-712 | Me | 5-Me | CH | OPr | H | |
| 1-713 | Me | 5-C1 | CH | OPr | H | |
| 1-714 | Me | 5-OMe | CH | OPr | H | |
| 1-715 | H | H | CH | OCH2CH=CH2 | H | |
| 1-716 | Me | 5-Me | CH | och2ch=ch2 | H | |
| 1-717 | Me | 5-C1 | CH | och2ch=ch2 | H | |
| 1-718 | Me | 5-OMe | CH | och2ch=ch2 | H | |
| 1-719 | H | H | CH | OBn | H | |
| 1-720 | Me | 5-Me | CH | OBn | H | |
| 1-721 | Me | 5-C1 | CH | OBn | H | |
| 1-722 | H | H | CH | OPh | H | 257-260 |
| 1-723 | H | H | CH | OPh(4-Cl) | H | |
| 1-724 | H | H. | CH | OPh(4-Me) | H | |
| 1-725 | H | H | CH | OPh(4-OMe) | H | |
| 1-726 | H | H | CH | OMe | Me | 107-110 |
| 1-727 | Me | H | CH | OMe | Me | |
| 1-728 | H | 5-C1 | CH | OMe | Me | |
| 1-729 | H | 5-Me | CH | OMe | Me | |
| 1-730 | H | 5-CF3 | CH | OMe | Me | |
| 1-731 | Me | 5-Cl | CH | OMe | Me | 124-127 |
| 1-732 | Me | 5-Me | CH | OMe | Me | |
| 1-733 | Me | 5-CF3 | CH | OMe | Me | |
| 1-734 | Me | 5-OMe | CH | OMe | Me | |
| 1-735 | Me | 6-C1 | CH | OMe | Me | |
| 1-736 | Me | 5,6-(OMe)2 | CH | OMe | Me | |
| 1-737 | Cl | 5-C1 | CH | OMe | Me | |
| 1-738 | Cl | 5-Me | CH | OMe | Me | |
| 1-739 | Cl | 5-OMe | CH | OMe | Me | |
| 1-740 | Cl | 5,6-(OMe)2 | CH | OMe | Me | |
| 1-741 | cf3 | 5-C1 | CH | OMe | Me | |
| 1-742 | cf3 | 5-Me | CH | OMe | Me |
«9 ···· • ·
(Tabulka23 )
| 1--------------- sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo RI ™ (¾20) | |
| 1-743 | cf3 | 5-OMe | CH | OMe | Me | ||
| 1-744 | Et | 5-C1 | CH | OMe | Me | ||
| 1-745 | Et | 5-Me | CH | OMe | Me | ||
| 1-746 | Et | 5-OMe | CH | OMe | Me | ||
| 1-747 | H | H | N | OMe | Me | ||
| 1-748 | H | 5-C1 | N | OMe | Me | ||
| 1-749 | H | 5-Me | N | OMe | Me | ||
| 1-750 | H | 5-CF3 | N | OMe | Me | ||
| 1-751 | Me | 5-C1 | N | OMe | Me | ||
| 1-752 | Me | 5-Me | N | OMe | Me | 124-127 | |
| 1-753 | Me | 5-CF3 | N | OMe | Me | ||
| 1-754 | Me | 5-OMe | N | OMe | Me | ||
| 1-755 | Me | 6-C1 | N | OMe | Me | ||
| 1-756 | Me | 5,6-(OMe)2 | N | OMe | Me | ||
| 1-757 | Cl | 5-C1 | N | OMe | Me | ||
| 1-758 | Cl | 5-Me | N . | OMe | Me | 117-120 | |
| 1-759 | Cl | 5-OMe | N | OMe | Me | ||
| 1-760 | Cl | 5,6-(OMe)2 | N | OMe | Me | ||
| 1-761 | cf3 | 5-C1 | N | OMe | Me | ||
| 1-762 | cf3 | 5-Me | N | OMe | Me | 117-120 | |
| 1-763 | cf3 | 5-OMe | N | OMe | Me | ||
| 1-764 | Et | 5-C1 | N | OMe | Me | ||
| 1-765 | Et | 5-Me | N | OMe | Me | ||
| 1-766 | Et | 5-OMe | N | OMe | Me | ||
| 1-767 | nh2 | 5-Me | N | OMe | Me | > 300 | |
| 1-768 | H | H | CH | OEt | Me | 57-60 | |
| 1-769 | Me | H | CH | OEt | Me | 92-94 | |
| 1-770 | cf3 | H | CH | OEt | Me | ||
| 1-771 | Cl | H | CH | OEt | Me | 95-96 | |
| 1-772 | H | 5-Me | CH | OEt | Me | 105-108 | |
| 1-773 | Me | 5-F | CH | OEt | Me | ||
| 1-774 | Me | 5-Cl | CH | OEt | Me | ||
| 1-775 | Me | 5-Me | CH | OEt | Me ' | 108-110 | |
| 1-776 | Me | 5-CF3 | CH | OEt | Me |
(Tabulka 24 )
| 1 sloučenině č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Sd20) | |
| 1-777 | Me | 5-OMe | CH | OEt | Me | ||
| 1-778 | Me | 5-CN | CH | OEt | Me | ||
| 1-779 | Me | 6-C1 | CH | OEt | Me | ||
| 1-780 | Me | 5,6-(OMe)2 | CH | OEt | Me | ||
| 1-781 | Cl | 5-Cl | CH | OEt | Me | ||
| 1-782 | Cl | 5-Me | CH | OEt | Me | ||
| 1-783 | Cl | 5-CF3 | CH | OEt | Me | ||
| 1-784 | Cl | 5-OMe | CH | OEt | Me | ||
| 1-785 | Cl | 5,6-(OMe)2 | CH | OEt | Me | ||
| 1-786 | CFg | 5-C1 | CH | OEt | Me | ||
| 1-787 | cf3 | 5-Me | CH | OEt | Me | 117-118 | |
| 1-788 | cf3 | 5-OMe | CH | OEt | Me | ||
| 1-789 | Et | 5-C1 | CH. | OEt | Me | ||
| 1-790 | Et | 5-Me | CH | OEt | Me | ||
| 1-791 | Et | 5-CF3 | CH | OEt | Me | ||
| 1-792 | Et | 5-OMe | CH | OEt | Me | ||
| 1-793 | H | H | N | OEt | Me | ||
| 1-794 | H | 5-Br | N | OEt | Me | ||
| 1-795 | Me | 5-C1 | N | OEt | Me | ||
| 1-796 | Me | 5-Br | N | OEt | Me | ||
| 1-797 | Me | 5-Me | N | OEt | Me | ||
| 1-798 | Me | 5-CF3 | N | OEt | Me | ||
| 1-799 | Cl | 5-C1 | N | OEt | Me | ||
| 1-800 | Cl | 5-Me | N | OEt | Me | ||
| 1-801 | cf3 | 5-C1 | N | OEt | Me | ||
| 1-802 | cf3 | 5-Br | N | OEt | ' Me | ||
| 1-803 | cf3 | 5-Me | N | OEt | Me | ||
| 1-804 | H | H | CH | OPr | Me | 47-50 | |
| 1-805 | H | 5-OMe | CH | OPr | Me | 100-102 | |
| 1-806 | Me | H | CH | OPr | Me | 75-78 | |
| 1-807 | cf3 | H | CH | OPr | Me | ||
| 1-808 | H | 5-C1 | CH | OPr | Me | ||
| 1-809 | H | 5-Me | CH | OPr | Me | 73-76 | |
| 1-810 | Me | 5-F | CH | OPr | Me |
(Tabulka 25 )
| I sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo (¾ ) | |
| 1-811 | Me | 5-C1 | CH | OPr | Me | 90-93 | |
| 1-812 | Me | 5-Me | CH | OPr | Me | 59-62 | |
| 1-813 | Me | 5-OMe | CH | OPr | Me | 99-101 | |
| 1-814 | Me | 6-C1 | CH | OPr | Me | 109-112 | |
| 1-815 | Me | 5,6-(OMe)2 | CH | OPr | Me | ||
| 1-816 | Cl | 5-C1 | . CH | OPr | Me | ||
| 1-817 | Cl | 5-Me | CH | OPr | Me | 76-77 | |
| 1-818 | Cl | 5-OMe | CH | OPr | Me | 87-90 | |
| 1-819 | Cl | 5,6-(OMe)2 | CH | OPr | Me | ||
| 1-820 | cf3 | 5-C1 | CH | OPr | Me | ||
| 1-821 | cf3 | 5-Me | CH | OPr | Me | ||
| 1-822 | cf3 | 5-CF3 | CH | OPr | Me | ||
| 1-823 | cf3 | 5-OMe | CH | OPr | Me | ||
| 1-824 | Et | 5-C1 | CH | OPr | Me | ||
| 1-825 | Et | • 5-Me | CH | OPr | Me | ||
| 1-826 | Et | 5-OMe | CH | OPr | Me | ||
| 1-827 | H | H | N | OPr | Me | ||
| 1-828 | H | 5-Br | N | OPr | Me | ||
| 1-829 | Me | 5-C1 | N | OPr | Me | ||
| 1-830 | Me | 5-Br | N | OPr | Me | ||
| 1-831 | Me | 5-Me | N | OPr | Me | 104-107 | |
| 1-832 | Me | 5-CF3 | N | OPr | Me | ||
| 1-833 | Cl | 5-C1 | N | OPr | Me | ||
| 1-834 | Cl | 5-Me | N | OPr | Me | ||
| 1-835 | cf3 | 5-C1 | N | OPr | Me | ||
| 1-836 | cf3 | 5-Br | N | OPr | Me | ||
| 1-837 | cf3 | 5-Me | N | OPr | Me | ||
| 1-838 | nh2 | 5-Me | N | OPr | Me | 152-153 | |
| 1-839 | H | H | CH | OPr-i | Me | 66-68 | |
| 1-840 | Me | H | CH | OPr-i | Me | 1.5805 | |
| 1-841 | cf3 | H | CH | OPr-i | Me | ||
| 1-842 | H | 5-C1 | CH | OPr-i | Me | ||
| 1-843 | H | 5-Me | CH | OPr-i | Me | ||
| 1-844 | Me . | 5-F | CH | OPr-i | Me |
• · ···· • · (Tabulka 26’)
I sloučenina
32_
m.p. (°C)
1.5795
73-76
| 1-845 | Me | 5-C1 | CH | OPr-i | Me |
| 1-846 | Me | 5-Me | CH | OPr-i | Me |
| 1-847 | Me | 5-OMe | CH | OPr-i | Me |
| 1-848 | Me | 6-C1 | CH | OPr-i | Me |
| 1-849 | Me | 5,6-(OMe)2 | CH | OPr-i | Me |
| 1-850 | Cl | 5-C1 | CH | OPr-i | Me |
| 1-851 | Cl | 5-Me | CH | OPr-i | Me |
| 1-852 | Cl | 5-CF3 | CH | OPr-i | Me |
| 1-853 | Cl | 5-OMe | CH | OPr-i | Me |
| 1-854 | Cl | 5,6-(OMe)2 | CH | OPr-i | Me |
| 1-855 | cf3 | 5-C1 | CH | OPr-i | Me |
| 1-856 | cf3 | 5-Me | CH | OPr-i | Me |
| 1-857 | cf3 | 5-OMe | CH | OPr-i | Me |
| 1-858 | Et | 5-C1 | CH | OPr-i | Me |
| 1-859 | Et | 5-Me | CH | OPr-i | Me |
| 1-860 | Et | 5-OMe | CH | OPr-i | Me |
| 1-861 | H | H | N | OPr-i | Me |
| 1-862 | H | 5-Br | N | OPr-i | Me |
| 1-863 | Me | 5-C1 | N | OPr-i | Me |
| 1-864 | Me | 5-Br | N | OPr-i | Me |
| 1-865 | Me | 5-Me | N | OPr-i | Me |
| 1-866 | Me | 5-CFs | N | OPr-i | Me |
| 1-867 | Cl | 5-C1 | N | OPr-i | Me |
| 1-868 | Cl | 5-Me | N | OPr-i | Me |
| 1-869 | cf3 | 5-C1 | N | OPr-i | Me |
| 1-870 | cf3 | 5-Br | N | OPr-i | Me |
| 1-871 | cp3 | 5-Me | N | OPr-i | Me |
| 1-872 | H | H | CH | OBu | Me |
| 1-873 | Me | H | CH | OBu | Me |
| 1-874 | Me | 5-C1 | CH | OBu | Me |
| 1-875 | Me | 5-Me | CH | OBu | Me |
| 1-876 | Me | 5-OMe | CH | OBu | Me |
| 1-877 | Cl | 5-C1 | CH | OBu | Me |
| 1-878 | Cl | 5-Me | CH | OBu | Me |
·· *·«· ·· 0
0 0 0 0··
0 0000 0· · • 0 00 0
0 0 · (Tabulka 27 )
| 1 sloučenina č. | X | Yn | A | R1 R2 | m.p. (°C) nebo RI (nD 20) | ||
| 1-879 | Cl | 5-OMe | CH | OBu Me | |||
| 1-880 | cf3 | 5-C1 | CH | OBu Me | |||
| 1-881 | cf3 | 5-Me | CH | OBu Me | |||
| 1-882 | cf3 . | 5-OMe | CH | OBu Me | |||
| 1-883 | H | H | CH | OCH2CH=CH2 Me | 55-58 | ||
| 1-884 | H | 5-Me | CH | OCH2CH=CH2 Me | |||
| 1-885 | Me | H | CH | OCH2CH=CH2 Me | 84-87 | ||
| 1-886 | Me | 5-C1 | CH | OCH2CH=CH2 Me | |||
| 1-887 | Me | 5-Me | CH | OCH2CH=CH2 Me | |||
| 1-888 | Me | 5-OMe | CH | OCH2CH=CH2 Me | |||
| 1-889 | Cl | 5-C1 | CH | OCH2CH=CH2 Me | |||
| 1-890 | Cl | 5-Me | CH | OCH2CH=CH2 Me | |||
| 1-891 | cf3 | 5-C1 | CH | OCH2CH=CH2 Me | |||
| 1-892 | cf3 | 5-Me | CH | OCH2CH=CH2 Me | |||
| 1-893 | cf3 | 5-OMe | CH | OCH2CH=CH2 Me | |||
| 1-894 | H | H | CH | OCH2CssCH Me | 145-148 | ||
| 1-895 | H | 5-Me | CH | OCH2C=CH Me | 183-186 | ||
| 1-896 | Me | H | CH | OCH2C=CH Me | 147-149 | ||
| 1-897 | Me | 5-C1 | CH | OCH2C=CH Me | |||
| 1-898 | Me | 5-Me | CH | OCH2C=CH Me | 147-150 | ||
| 1-899 | Me | 5-OMe | CH | OCH2C=CH Me | |||
| 1-900 | Cl | 5-C1 | CH | OCH2C=CH Me | |||
| 1-901 | Cl | 5-Me | CH | OCH2CsCH Me | |||
| 1-902 | cf3 | 5-C1 | CH | OCH2C=CH Me | |||
| 1-903 | cf3 | 5-Me | CH | OCH,C=CH Me | 113-116 | ||
| 1-904 | nh2 | 5-Me | CH | OCH2C=CH Me | 225-228 | ||
| 1-905 | H | H | CH | OBn Me | |||
| 1-906 | H | H | CH | OPn-c Me | 1.5965 | ||
| 1-907 | Me | H | CH | OPn-c Me | 1.5941 | ||
| 1-908 | Me | 5-C1 | CH | OPn-c Me | |||
| 1-909 | Me | 5-C1 | N | OPn-c Me | |||
| 1-910 | H | H | CH | SMe Me | |||
| 1-911 | Me | H | CH | SMe Me | 139-142 | ||
| 1-912 | Me | 5-Me | CH | SMe Me |
···· • ·
m.p. (°C) (Tabulka 28 )
| č. | λ in λ rc κ | |||||
| 1-913 | Me | 5-C1 | CH | SMe | Me | |
| 1-914 | H | H | N | SMe | Me | |
| 1-915 | Me | 5-Me | N | SMe | Me | 134-137 |
| 1-916 | Me | 5-C1 | N | SMe | Me | |
| 1-917 | H | H | CH | OMe | Et | |
| 1-918 | Me | 5-Me | CH | OMe | Et | |
| 1-919 | Me | 5-C1 | CH | OMe | Et | |
| 1-920 | Me | 5-CF3 | CH | OMe | Et | |
| 1-921 | Me | 5-OMe | CH | OMe | Et | |
| 1-922 | Cl | 5-Me | CH | OMe | Et | |
| 1-923 | Cl | 5-C1 | CH | OMe | Et | |
| 1-924 | H | H | CH | OEt | Et | |
| 1-925 | Me | 5-Me | CH | OEt | Et | |
| 1-926 | Me | 5-C1 | CH | OEt | Et | |
| 1-927 | Me | 5-CF3 | CH | OEt | Et | |
| 1-928 | Me | 5-OMe | CH | OEt | Et | |
| 1-929 | Cl | 5-Me | CH | OEt | Et | |
| 1-930 | Cl | 5-C1 | CH | OEt | Et | |
| 1-931 | H | H | CH | OPr | Et | |
| 1-932 | Me | 5-Me | CH | OPr | Et | |
| 1-933 | Me | 5-C1 | CH | OPr | Et | |
| 1-934 | Me | 5-CF3 | CH | OPr | Et | |
| 1-935 | Me | 5-OMe | CH | OPr | Et | |
| 1-936 | Cl | 5-Me | CH | OPr | Et | |
| 1-937 | Cl | 5-C1 | CH | OPr | Et | |
| 1-938 | H | H | N | OMe | Et | |
| 1-939 | H | 5-Br | N | OMe | Et | 125-128 |
| 1-940 | Me | 5-Me | N | OMe | Et | |
| 1-941 | Me | 5-C1 | N | OMe | Et | 134-137 |
| 1-942 | Me | 5-Br | N | OMe | Et | 134-141 |
| 1-943 | Cl | 5-Me | N | OMe | Et | |
| 1-944 | Cl | 5-C1 | N | OMe | Et | |
| 1-945 | cf3 | 5-Me | N | OMe | Et | 86-89 |
| 1-946 | cf3 | 5-C1 | N | OMe | Et | 79-82 |
| • · | • | 99 | 9999 | 9 9 | 9 | |||
| e | 9 | • | 9 | 9 | 9 | 9 | 9 | 9 9 |
| • | 9 | 9 9 | 9 | 9 | 9 | • · | 9 | |
| • | 9 | 9999 | 9 9 | 9 | 9 | • · | 9 | 9 |
| 9 | 9 | 9 | 9 | 9 | 9 | • | 9 | 9 |
| 99 | 9 | 99 | 9 | 99 | 99 9 |
(Tabulka 29 )
| 1------------ sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Sd20) | |
| 1-947 | cf3 | 5-Br | N | OMe | Et | 97-100 | |
| 1-948 | H | H | N | OEt | Et | ||
| 1-949 | H | 5-Br | N | OEt | Et | 79-82 | |
| 1-950 | Me | 5-Me | N | OEt | Et | ||
| 1-951 | Me | 5-C1 | N | OEt | Et | ||
| 1-952 | Me | 5-Br | N | OEt | Et | 96-98 | |
| 1-953 | Cl | 5-Me | N | OEt | Et | ||
| 1-954 | Cl | 5-C1 | N | OEt | Et | ||
| 1-955 | cf3 | 5-Me | N | OEt | Et | ||
| 1-956 | cf3 | 5-C1 | N | OEt | Et | 66-67 | |
| 1-957 | cf3 | 5-Br | N | OEt | Et | 97-100 | |
| 1-958 | H | H | CH | OMe | Pr | 78-80 | |
| 1-959 | Me | H | CH | OMe | Pr | 1.5892 | |
| 1-960 | Cl | H | CH | OMe | Pr | 1.6009 | |
| 1-961 | H | 5-C1 | CH | OMe | Pr | ||
| 1-962 | H | 5-Me | CH | OMe | Pr | 116-119 | |
| 1-963 | Me | 5-F | CH | OMe | Pr | ||
| 1-964 | Me | 5-C1 | CH | OMe | Pr | 113-116 | |
| 1-965 | Me | 5-Me | CH | OMe | Pr | 105-107 | |
| 1-966 | Me | 5-OMe | CH | OMe | Pr | ||
| 1-967 | Me | 6-C1 | CH | OMe | Pr | 68-71 | |
| 1-968 | Cl | 5-C1 | CH | OMe | Pr | ||
| 1-969 | Cl | 5-Me | CH | OMe | Pr | ||
| 1-970 | Cl | 5-OMe | CH | OMe | Pr | ||
| 1-971 | cf3 | 5-C1 | CH | OMe | Pr | ||
| 1-972 | cf3 | 5-Me | CH | OMe | Pr | ||
| 1-973 | cf3 | 5-OMe | CH | OMe | Pr | ||
| 1-974 | H | H | CH | OEt | Pr | ||
| 1-975 | H | 5-C1 | CH | OEt | Pr | ||
| 1-976 | H | 5-Me | CH | OEt | Pr | ||
| 1-977 | Me | 5-F | CH | OEt | Pr | ||
| 1-978 | Me | 5-C1 | CH | OEt | Pr | ||
| 1-979 | Me | 5-Me | CH | OEt | Pr | ||
| 1-980 | Me | 5-CF3 | CH | OEt | Pr |
·· · ♦ · ·· • ·
(Tabulka 30 )
| 1 sloučením č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ůt20) | |
| 1-981 | Me | 5-OMe | CH | OEt | Pr | ||
| 1-982 | Cl | 5-Cl | CH | OEt | Pr | ||
| 1-983 | Cl | 5-Me | CH | OEt | Pr | ||
| 1-984 | Cl | 5-CF3 | . CH | OEt | Pr | ||
| 1-985 | Cl | 5-OMe | CH | OEt | Pr | ||
| 1-986 | cf3 | 5-C1 | CH | OEt | Pr | ||
| 1-987 | cf3 | 5-Me | CH | OEt | Pr | ||
| 1-988 | cf3 | 5-OMe | CH | OEt | Pr | ||
| 1-989 | H | H | CH | OPr | Pr | ||
| 1-990 | Me | 5-Me | CH | OPr | Pr | ||
| 1-991 | Me | 5-C1 | CH | OPr | Pr | ||
| 1-992 | Me | 5-OMe | CH | OPr | Pr | ||
| 1-993 | Cl | 5-Me | CH | OPr | Pr | ||
| 1-994 | Cl | 5-C1 | CH | OPr | Pr | ||
| 1-995 | H | H | N | OMe | Pr | ||
| 1-996 | H | 5-Br | N | OMe | Pr | ||
| 1-997 | Me | 5-C1 | N | OMe | Pr | ||
| 1-998 | Me | 5-Br | N | OMe | Pr | ||
| 1-999 | Me | 5-Me | N | OMe | Pr | 112-115 | |
| 1-1000 | Cl | 5-C1 | N | OMe | Pr | ||
| 1-1001 | Cl | 5-Me | N | OMe | Pr | ||
| 1-1002 | cf3 | 5-C1 | N | OMe | Pr | ||
| 1-1003 | cf3 | 5-Br | N | OMe | Pr | ||
| 1-1004 | cf3 | 5-Me | N | OMe | Pr | 92-95 | |
| [-1005 | H | H | N | OEt | Pr | ||
| [-1006 | H | 5-Br. | N | OEt | Pr | ||
| [-1007 | Me | 5-C1 | N | OEt | Pr | ||
| [-1008 | Me | 5-Br | N | OEt | Pr | ||
| [-1009 | Me | 5-Me· | N | OEt | Pr | ||
| -1010 | Cl | 5-C1 | N | OEt | Pr | ||
| -1011 | Cl | 5-Me | N | OPr | Pr | ||
| -1012 | cf3 | 5-C1 | N | OPr | Pr | ||
| -1013 | cf3 | 5-Br | N | OPr | Pr | ||
| I | -1014 | cf3 | 5-Me | N | OPr | Pr |
·· «··♦
37(Tabulka 31 )
| 1 sloučenin. | 1 X | Yn | A | R1 | R2 | m.p. (°C) nebo Ti20) | |
| č. | |||||||
| 1-101 | 5 H | H | N | OMe | Pr-c | ||
| 1-101 | 6 H | 5-Br | N | OMe | Pr-c | 154-157 | |
| Ι-1ΟΓ | Me | 5-C1 | N | OMe | Pr-c | 116-119 | |
| I-101Í | Me | 5-Br | N | OMe | Pr-c | 121-124 | |
| I-1O1Í | Me | 5-Me | N | OMe | Pr-c | 167-170 | |
| 1-102( | cf3 | 5-C1 | N | OMe | Pr-c | 101-104 | |
| 1-102] | cf3 | 5-Br | N | OMe | Pr-c | 119-122 | |
| 1-1022 | cf3 | 5-Me | N | OMe | Pr-c | 116-119 | |
| 1-1023 | H | H | N | OEt | Pr-c | ||
| 1-1024 | H | 5-Br | N | OEt | Pr-c | 137-140 | |
| 1-1025 | Me | 5-C1 | N | OEt | Pr-c | 130-133 | |
| 1-1026 | Me | 5-Br | N | OEt | Pr-c | 124-127 | |
| 1-1027 | Me | 5-Me | N | OEt | Pr-c | 131-133 | |
| 1-1028 | cf3 | 5-C1 | N | OEt | Pr-c | 82-85 | |
| 1-1029 | cf3 | 5-Br | N | OEt | Pr-c | 105-108 | |
| 1-1030 | cf3 | 5-Me | N | OEt | Pr-c | 79-82 | |
| 1-1031 | H | H | N | SMe | Pr-c | ||
| 1-1032 | H | 5-Br | N | SMe | Pr-c | ||
| 1-1033 | Me | 5-C1 | N | SMe | Pr-c | ||
| 1-1034 | Me | 5-Br | N | SMe | Pr-c | ||
| 1-1035 | Me | 5-Me | N | SMe | Pr-c | ||
| 1-1036 | cf3 | 5-C1 | N | SMe | Pr-c | ||
| 1-1037 | cf3 | 5-Br | N | SMe | Pr-c | ||
| [-1038 | cf3 | 5-Me | N | SMe | Pr-c | ||
| [-1039 | Me | H | CH | SMe | SMe | 129-131 | |
| [-1040 | H | 5-C1 | N | SMe | SMe | ||
| -1041 | H | 5-Br | N | SMe | SMe | ||
| -1042 | Me | H | N | SMe | SMe | 176-179 | |
| -1043 | Me | 5-C1 | N | SMe | SMe | 186-189 | |
| I | -1044 | Me | 5-Br | N | SMe | SMe | |
| I | -1045 | Me | 5-Me | N | SMe | SMe | |
| I | -1046 | cf3 | 5-C1 | N | SMe | SMe | 144-146 |
| I | -1047 | cf3 | 5-Br | N | SMe | SMe | |
| I | -1048 | cf3 | 5-Me | N | SMe | Me | 106-109 |
·· «·«· (Tabulka 32 )
| Vl~~ sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ri (nD 20) | |
| 1-104 | 9 H | 5-Br | N | OMe | SMe | ||
| 1-105 | 0 Me | 5-C1 | N | OMe | SMe | ||
| 1-105 | 1 Me | 5-Br | N | OMe | SMe | ||
| 1-105 | 2 Me | 5-Me | N | OMe | SMe | ||
| 1-105. | 3 CF3 | 5-C1 | N | OMe | SMe | ||
| 1-105' | cf3 | 5-Br | N | OMe | SMe | ||
| I-105E | cf3 | 5-Me | N | OMe | SMe | ||
| I-105€ | H | H | CH | OMe | Ph | 160-162 | |
| 1-1051 | H | H | N | OMe | Ph | ||
| 1-1058 | Me | 5-Me | N | OMe | Ph | 165-168 | |
| I-105S | cf3 | 6-Me | N | OMe | Ph | 150-153 | |
| 1-1060 | H | H | CH | Cl | Ph | 176-179 | |
| 1-1061 | H | H | N | Cl | Ph | ||
| [-1062 | H | H | CH | Cl | Cl | 165-168 | |
| 1-1063 | Me | H | CH | Cl | Cl | 170-172 | |
| 1-1064 | Me | 5,6-Cl2 | CH | Cl | Cl | 202-205 | |
| 1-1065 | H | H | N | Cl | Cl | ||
| 1-1066 | Me | H | N | Cl | Cl | > 300 | |
| 1-1067 | H | H | CH | Cl | Me | 187-190 | |
| 1-1068 | Me | H | CH | Cl | Me | 122-125 | |
| 1-1069 | H | H | CH | Cl | ' N(Me)2 | 205-208 | |
| 1-1070 | H | H | N | Cl | N(Me)2 | ||
| 1-1071 | Me | 5-C1 | N | N(Me)2 | N(Me)2 | 203-206 | |
| [-1072 | H | H | CH | OMe | N(Me)2 | 129-132 | |
| [-1073 | H | H | CBr | OMe | OMe | >300 | |
| r-1074 | H | H | CMe | OMe | OMe | 152-155 | |
| -1075 | H | H | CMe | Cl | Cl | 184-187 | |
| -1076 | H | H | COMe | H | H | 131-134 | |
| -1077 | Me | 5-Me | COMe | H | H | ||
| I | -1078 | Me | 5-C1 | COMe | H | H | |
| I | -1079 | H | H | CH | Me | Me | 131-132 |
| I | -1080 | Me | 5-C1 | CH | Me | Me | 138-140 |
| I | -1081 | Me | 5-CF3 | CH | Me | Me | |
| I | -1082 | H | H | CH | Me | CFS | 107-110 |
·· ·Φ·4 ( Tabulka 33 ) |m.p. (°C)
X Υη AR1 r2 nebo
| 1-1081 | Me | 5-C1 | CH | Me | cf3 | |
| 1-108^ | Me | 5-C1 | N | Me | cf3 | |
| 1-1081 | H | H | CH | Me | Et | 60-63 |
| 1-1086 | H | 5-Me | CH | Me | Et | 55-58 |
| 1-1087 | Me | 5-Me | CH | Me | Et | 109-112 |
| 1-1088 | Me | 5-C1 | CH | Me | Et | 76-79 |
| I-108S | Me | 5-OMe | CH | Me | Et | |
| 1-1090 | Me | 6-C1 | CH | Me | Et | 84-87 |
| 1-1091 | Cl | 5-C1 | CH | Me | Et | |
| 1-1092 | Cl | 5-Me | CH | Me | Et | |
| 1-1093 | H | H | CH | Et | Et | 58-61 |
| 1-1094 | H | 5-Me | CH | Et | Et | 68-71 |
| 1-1095 | Me | 5-Me | CH | Et | Et | 76-79 |
| 1-1096 | Me | 5-C1 | CH | Et | Et | 78-80 |
| 1-1097 | Me | 5-OMe | CH | Et | Et | |
| 1-1098 | Me | 6-C1 | CH | Et | Et | 80-83 |
| 1-1099 | Cl | 5-C1 | CH | Et | Et | |
| 1-1100 | Cl | 5-Me | CH | Et | Et | |
| 1-1101 | H | H | CH | Me | Pr-c | 124-125 |
| 1-1102 | H | 5-Mé | CH | Me | Pr-c | |
| 1-1103 | Me | 5-Me | CH | Me | Pr-c | 153-156 |
| 1-1104 | Me | 5-C1 | CH | Me | Pr-c | 119-122 |
| 1-1105 | Me | 5-OMe | CH | Me | Pr-c | |
| 1-1106 | Me | 6-C1 | CH | Me | Pr-c | 110-113 |
| 1-1107 | Cl | 5-C1 | CH | Me | Pr-c | |
| 1-1108 | Cl | 5-Me | CH | Me | Pr-c | |
| 1-1109 | H | H | CH | Et | Pr-c | |
| 1-1110 | Me | 5-Me | CH | Et | Pr-c | |
| 1-1111 | Me | 5-C1 | CH | Et | Pr-c | |
| 1-1112 | Me | 5-OMe | CH | Et | Pr-c | |
| [-1113 | Me | 6-C1 | CH | Et | Pr-c | |
| 1-1114 | Cl | 5-C1 | CH | Et | Pr-c | |
| [-1115 | Cl | 5-Me | CH | Et | Pr-c | |
| [-1116 | H | H | CH | Et | Et |
·· ···· ·· · • · · ·· • · · ® ·· • · ···· · ·· • · · ·· φ· ··· «· • · ♦· • ·· • · · * • ·· • «· · (Tabulka 34 )
| 1 sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo (ío20) | |
| Ι-11Γ | Me | 5-Me | CH | Et | Et | ||
| I-111E | Me | 5-C1 | CH | Et | Et | ||
| r-nis | Me | 5-OMe | CH | Et | Et | ||
| I-112C | Me | 6-Cl | CH | Et | Et | ||
| 1-1121 | Cl | 5-C1 | CH | Et | Et | ||
| 1-1122 | Cl | 5-Me | CH | Et | Et | ||
| 1-1123 | H | H | CH | CsCMe | Me | 134-136 | |
| 1-1124 | Me | 5-Me | CH | C=CMe | Me | ||
| 1-1125 | Me | 5-C1 | CH | CsCMe | Me | ||
| 1-1126 | Me | 5-Me | N | C = CMe | Me | ||
| 1-1127 | Me | 5-C1 | N | C=CMe | Me | ||
| 1-1128 | Cl | 5-C1 | CH | C = CMe | Me | ||
| 1-1129 | Cl | 5-Me | CH | C=CMe | Me | ||
| 1-1130 | H | H | CH | CH=CH2 | Me | ||
| 1-1131 | Me | 5-Me | CH | ch=ch2 | Me | ||
| 1-1132 | Me | 5-C1 | CH | ch=ch2 | Me | ||
| 1-1133 | Me | 5-Me | N | ch=ch2 | Me | ||
| 1-1134 | Cl | 5-C1 | CH | ch=ch2 | Me | ||
| 1-1135 | Cl | 5-Me | CH | ch=ch2 | Me | ||
| 1-1136 | H | H | CH | CHO | . Me | ||
| 1-1137 | Me | 5-C1 | CH | CHO | Me | ||
| 1-1138 | Me | 5-C1 | N | CHO | Me | ||
| 1-1139 | H | H | CH | COMe | Me | ||
| 1-1140 | Me | 5-C1 | CH | COMe | Me | ||
| 1-1141 | Me | 5-C1 | N | COMe | Me | ||
| 1-1142 | H | H | CH | CH2OMe | Me | ||
| [-1143 | Me | 5-C1 | CH | CH2OMe | Me | ||
| [-1144 | Me | 5-Me | CH | CH2OMe | Me | ||
| [-1145 | H | H | N | CH2OMe | OMe | ||
| [-1146 | Me | H | CH | CN | CN | ||
| [-1147 | Me | H | CH | CN | Me · | 187-189 | |
| [-1148 | Me | H | N | CN | CN | ||
| [-1149 | Me | H | N | CN | Me | ||
| [-1150 | Me | H | CH | SO2Me | SO2Me |
Μ ( Tabulka 35 )
| J sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo RT AA (no20) | |
| c. | |||||||
| 1-1151 | Me | H | N | SO2Me | SO2Me | ||
| 1-1152 | Me | H | CH | SO2Me | Me | 183-186 |
Typické postupy produkce derivátů pyrimidinylbenzimidazolu a triazinylbenzimidazolu, reprezentované obecným vzorcem I, jakožto sloučenin předkládaného vynálezu, budou uvedeny níže v příkladech.
Postup 1
Nx NH
II
III
Zásada
------->
Rozpouštědlo
I
2 (kde X, Y, R , R , A a n mají stejný význam jak bylo zmiňováno výše, resp., a L je odpadová skupina jako je atom halogenu, (Ci-C6) alkylsulfonylová skupina nebo benzylsulfonylová skupina.)
Sloučenina podle předkládaného vynálezu, reprezentovaná obecným vzorcem I, je produkována reakcí derivátu benzimidazolu, reprezentovaného obecným vzorcem II, a derivátu pyrimidinu nebo derivátu triazinu, reprezentovaného obecným vzorcem III, v přítomnosti zásady v rozpouštědle. Jako zásady zde lze použít například uhličitan, hydrogenuhličitan, acetát, nasycený alkoholem, hydroxid, hydrid nebo oxid zásaditých kovů nebo alkalických půdních kovů, obzvláště sodíku, draslíku, hořčíku nebo vápníku. Rozpouštědlo, které může být v uvedené reakci použito, je takové, které neinhibuje postup uvedené reakce, a použit může být například ether jako je diethylether, diisopropylether, tetrahydrofuran, dioxan, monoglyme nebo diglyme, halogenovaný uhlovodík jako je dichlorethan, chloroform, chlorid uhličitý nebo tetrachlorethan, aromatický uhlovodík jako je benzen, chlorbenzen, nitrobenzen nebo toluen, nebo N,N-dimethylformamide, N,N-dimethylformamid, Ν,Ν-dimethylacetoamid, l,3-dimethyl-2-imidazolinon nebo dimethylsulfoxid. Tato inertní rozpouštědla mohou být použita samotná nebo jako směs. Reakčni teplota je vybrána v rozmezí od -20 °C až kbodu varu inertního rozpouštědla, které má být použito, a výhodněji v rozmezí od 0 °C do 80 °C. Reakčni čas se mění například v závislosti na reakčni teplotě nebo na reakčním množství, ale obecně může být vybráno v rozmezí od 1 hodiny až do 48 hodin. Po dokončení reakce je požadovaný produkt izolován z reakčního systému konvenčními metodami a může být purifikován například na chromatografické koloně nebo rekrystalizací, podle toho, co vyžaduje ten který případ.
Zde je derivát benzimidazolu, reprezentovaný obecným vzorcem II, komerčně dostupným produktem nebo je produkován známou metodou (například metodou odhalenou v Angewandte ·· · · í · · ·····
L·s ···· ·· «· τ J ············ ·· · ··· ··
Chemie, vol. 85, str. 866 (1973)); Journal of Američan Chemical Society, vol. 69, str. 2459 (1947);, Journal of the Američan Chemical Society, vol. 82, str. 3138 (1960); Organic Synthese, vol. 2, str. 65, (1943); nebo Organic Syntheses, vol. 4, str. 569 (1963)).
Postup 2.
rozpouštědlo
IV
R1
Acylující látka XCOHN NH-4 A
Cyklizace
I (kde X, Y, R , R , A a n mají stejný význam jak bylo zmiňováno výše, resp.).
Derivát anilidu reprezentovaný obecným vzorcem V může být produkován reakcí anilinopyrimidinu nebo derivátu anilinotriazinu reprezentovaného obecným vzorcem IV s acylující látkou v inertním rozpouštědle. Reakce je výhodně prováděná v přítomnosti zásady. Jako acylační látka může být zmíněn kyselý halid jako je acetyl chlorid, propionyl chlorid nebo benzoyl chlorid nebo kyselý anhydrid jako je anhydrid kyseliny trifluoroctové, anhydrid kyseliny propionové nebo anhydrid kyseliny benzoové. Inertní rozpouštědlo, které může být použito v uváděné reakci je takové, které neinhibuje postup uváděné reakce a může jít například o keton jako je aceton methylethyl keton nebo cyklohexanon, ether jako je diethyl ether, diisopropyl ether, tetrahydrofuran, dioxan, monoglym nebo diglym, a ester jako je ethyl acetát nebo methyl acetát, halogenovaný uhlovodík jako je dichlorethan, chloroform, chlorid uhličitý nebo tetrachlorethan, aromatický uhlovodík jako je benzen, chlorbenzen, nitrobenzen nebo toluen, nitril jako je acetonitril nebo N, N- dimethylformamid, N,N--dimethylacetooamid, 1, 3-dimethyl-2-imidazolinon, dimethylsulfoxid, pyridin nebo voda. Tyto inertní rozpouštědla mohou být použita samotná nebo smíšená. Jako zásada se v uváděné reakci používá anorganická báze nebo organická báze. Jako anorganická báze například uhličitan nebo hydroxid alkalických kovů nebo kovů alkalických zemin jako je uhličitan sodný, uhličitan draselný, uhličitan vápenatý, hydrogenuhličitan sodný, hydroxid sodný, hydroxid draselný nebo hydroxid vápenatý nebo hydrid alkalických kovů jako je hydrid lithný nebo hydrid sodný, jako organické zásady může být použit triethylamin, diisopropylethylamin nebo pyridin. Reakční teplota může být vybrána v rozmezí od -20 °C až k bodu varu inertního rozpouštědla, které má být použito a výhodně je tato teplota od 0 °C do 50 °C. Reakční čas se liší v závislosti například na teplotě reakce a na reakčním množství, ale může být vybrán v rozmezí od několika minut až do 48 hodin.
• ·
LlIí · · · · ·· · · τγ · · ···· · · · · · · • · · · · · ··
Potom je derivát anilidu reprezentovaný obecným vzorcem V vystaven cyklizační reakci bez rozpouštědla nebo v rozpouštědle v přítomnosti katalyzátoru, pokud to případ vyžaduje, aby vznikla sloučenina podle obecného vzorce I dle předkládaného vynálezu. Jako katalyzátor zde může být použita anorganická kyselina jako je kyselina sírová nebo kyselina chlorovodíková nebo organická kyselina jako je kyselina para-toluensulfonová, jako rozpouštědla mohou být v uvedené reakci použita ta rozpouštědla, která jsou uvedena v Postupu 1. Reakční teplota může být vybrána v rozmezí od 0 °C až k bodu varu rozpouštědla, které má být použito, a výhodně v rozmezí od laboratorní teploty kbodu varu rozpouštědla. Reakční čas se liší v závislosti například na reakční teplotě a reakčním množství, ale může být vybrán v rozmezí od 1 hodiny do 48 hodin. Po dokončení reakce je požadovaný produkt izolován zreakčního systému konvenčními metodami a může být purifíkován například na chromatografické koloně nebo rekrystalizací, jak případ vyžaduje.
Postup 3
IV I (Kde X, Y, Rl, R2, A a n mají stejný význam jak bylo uvedeno výše.)
Sloučenina dle předkládaného vynálezu reprezentovaná obecným vzorcem I může být produkována přímo zahřáním derivátu anilinopyrimidinu nebo derivátu anilinotriazinu reprezentovaným obecným vzorcem IV v karboxylové kyselině reprezentované obecným vzorcem VI, v přítomnosti anhydridu kyseliny, pokud to případ vyžaduje. Reakční teplota může být vybrána v rozmezí od 0 °C do bodu varu karboxylové kyseliny, která má být použita, výhodně jev rozmezí od laboratorní teploty k bodu varu karboxylové kyseliny. Reakční čas může být obecně vybrán v rozmezí od 1 hodiny do 48 hodin. Po dokončení reakce je požadovaný produkt izolován z reakčního systému konvenčními metodami a může být purifíkován například na chromatografické koloně nebo rekrystalizací, jak vyžaduje případ.
Postup 4
(Kde Y, Rl, R2, A a n mají stejný význam jak bylo uvedeno výše.)
Sloučenina reprezentovaná obecným vzorcem I-a může být produkována reakcí derivátu anilinopyrimidinu nebo derivátu anilinotriazinu reprezentovaného obecným vzorcem IV a reakční látky podle obecného vzorce VII jako je například BrCN nebo H2NCN metodou známou z literatury [například metoda odhalená v Joumal of the Američan Chemical Society, vol 69, str. 2459 (1947); nebo Angewandte Chemie, vol 85, str. 866 (1973)] v rozpouštědle. Jako rozpouštědlo, které může být použito v uvedené reakci se může použít rozpouštědel uvedených v Postupu 1. Reakční teplota může být vybrána v rozmezí od -20 °C do bodu varu reakční směsi, která má být použita, výhodně v rozmezí od 0 °C do bodu varu reakční směsi. Reakční čas se liší v závislosti například na reakční teplotě nebo reakčním množství,a může být vybrán v rozmezí obecně od 1 hodiny do 48 hodin. Po ukončení reakce je požadovaný produkt izolován v reakčním systému konvenčními metodami a může být purifikován například na chromatografické koloně nebo rekrystalizací, jak případ vyžaduje.
Postup 5
I-a I-d · .
(Kde X, je atom halogenu a Y, R , R , A a n mají stejný význam jak bylo uvedeno výše.)
Sloučenina reprezentovaná obecným vzorcem I-d je produkována diazotační reakcí derivátu 2-aminobenzimidazolu reprezentovaného obecným vzorcem I-a známou metodou (Sandmeyerova metoda, Schwechtenova metoda nebo Gattermanova metoda) v rozpouštědle při *·· ·· · · · · · • · · · · · · · · · • ····· ··«· · · · · • · · ··· ··· • · « a · · · a aaa reakční teplotě, která je normálně využívána, následována halogenací. Po ukončení reakce je požadovaný produkt izolován z reakčního systému konvenční metodou a může být purifikován například na chromatografické koloně nebo rekrystalizací, jak případ vyžaduje.
(Kde Y, R1, R2, A a n mají stejný význam jak bylo uvedeno výše, a R4 je Ci-Cg alkylová skupina.)
Sloučenina reprezentovaná obecným vzorcem I-e může být produkována oxidací derivátu pyrimidynilbenzimidazolu nebo derivátu triazinylbenzimidazolu reprezentovaného obecným vzorcem I-b známou metodou. Po dokončení reakce se požadovaný produkt izoluje z reakčního systému konvenční metodou a může být purifikován například na chromatografické koloně nebo rekrystalizací, jak případ vyžaduje. Oxidující látkou, která může být k přikládané reakci použita, je například peroxid vodíku nebo organická per-kyselina jako je m-chloroperbenzoová kyselina. Jako rozpouštědlo, které může být použito lze použít rozpouštědel uvedených v Postupu 1. Reakční teplota může být vybrána v rozmezí od - 20 °C až k bodu varu reakční směsi, která je použita, výhodně v rozmezí od 5 °C kbodu varu reakční směsi. Po ukončení reakce se požadovaný produkt izoluje z reakčního systému konvenční metodou a může být purifikován například na chromatografické koloně nebo rekrystalizací, jak případ vyžaduje.
(Tabulka 36 )
| cenina v c. | X | Yn | A | R1 | R2 | m.p. (°C) nebo út20) |
| 1-1 | H | H | CH | OMe | OMe | |
| 1-2 | Me | H | CH | OMe | OMe | |
| 1-3 | Et | H | CH | OMe | OMe | |
| 1-4 | Pr | H | CH | OMe | OMe | |
| 1-5 | Pr-i | H | CH | OMe | OMe | |
| 1-6 | Pr-c | H | CH | OMe | OMe | |
| 1-7 | Bu | H | CH | OMe | OMe | |
| 1-8 | Bn | H | CH | OMe | OMe | 169-172 |
| 1-9 | Bn(4-Cl) | H | CH | OMe | OMe | 187-200 |
| 1-10 | Bn(4-Me) | H | CH | OMe | OMe | 157-158 |
| 1-11 | Bn(4-OMe)H | CH | OMe | OMe | ||
| 1-12 | ch=ch2 | H | CH | OMe | OMe | 147-149 |
| 1-13 | CsCH | H | CH | OMe | OMe | |
| 1-14 | CH2OEt | H | CH | OMe | OMe | |
| 1-15 | CH2C1 | H | CH | OMe | OMe | 125-126 |
| 1-16 | ch2ch2ci h | CH | OMe | OMe | 162-165 | |
| 1-17 | ch2i | H | CH | OMe | OMe | |
| 1-18 | CC13 | H | CH | OMe | OMe | |
| 1-19 | cf3 | H | CH | OMe | OMe | |
| 1-20 | c,fs | H | CH | OMe | OMe | 82-85 |
| 1-21 | Ph | H | CH | OMe | OMe | 148-152 |
| 1-22 | Ph(4-Cl) | H | CH | OMe | OMe | |
| 1-23 | Ph(4-Me) | H | CH | OMe | OMe | |
| 1-24 | Ph(4-OMe) H | CH | OMe | OMe | ||
| 1-25 | H | H | N | OMe | OMe | |
| 1-26 | Me | H | N | OMe | OMe |
·♦·· (Tabulka 37 ) sloučenina
| č. | X | Yn | A |
| 1-27 | Et | H | N |
| 1-28 | Pr | H | N |
| 1-29 | Pr-i | H | N |
| 1-30 | Pr-c | H | N |
| 1-31 | Bu | H | N |
| 1-32 | Bn | H | N |
| 1-33 | Bn(4-Cl) | H | N |
| 1-34 | Bn(4-Me) | H | N |
| 1-35 | Bn(4-OMe | )H | N |
| 1-36 | ch=ch2 | H | N |
| 1-37 | C=CH | H | N |
| 1-38 | CH2OEt | H | N |
| 1-39 | CH2C1 | H | N |
| 1-40 | ch2i | H | N |
| 1-41 | CC13 | H | N |
| 1-42 | cf3 | H | N |
| 1-43 | c2f5 | H | N |
| 1-44 | Ph | H | N |
| 1-45 | Ph(4-Cl) | H | N |
| 1-46 | Ph(4-Me) | H | N |
| 1-47 | Ph(OMe) | H | N |
| 1-48 | H | 6-Me | CH |
| 1-49 | H | 6-Cl | CH |
| 1-50 | H | 5-F | CH |
| 1-51 | H | 5-C1 | CH |
| 1-52 | H | 5-Br | CH |
| 1-53 | H | 5-Me | CH |
| 1-54 | H | 5-Bu-t | CH |
| 1-55 | H | 5-CF3 | CH |
| 1-56 | H | 5-OMe | CH |
| 1-57 | H | 5-OEt | CH |
| 1-58 | H | 5-OPr | CH |
| 1-59 | H | 5-OCF3 | CH |
| R1 | R2 | m.p. (°C) nebo RI -a (¾20) |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe |
•f ·· 9· • · • · t • · · ·· ( Tabulka 38 )
X Yn
A R1
R2
| 1-60 | H | 5-OCH2CH=CH2 | CH | OMe | OMe |
| 1-61 | H | 5-OCH2C=CH | CH | OMe | OMe |
| 1-62 | H | 5-OPh | CH | OMe | OMe |
| 1-63 | H | 5-OPh(4-Cl) | CH | OMe | OMe |
| 1-64 | H | 5-OPh(4-Me) | CH | OMe | OMe |
| 1-65 | H | 5-OPh(4-OMe) | CH | OMe | OMe |
| 1-66 | H | 5-SMe | CH | OMe | OMe |
| 1-67 | H | 5-CH2OMe | CH | OMe | OMe |
| 1-68 | H | 5-COMe | CH | OMe | OMe |
| 1-69 | H | 5-COPh | CH | OMe | OMe |
| 1-70 | H | 5-CO2Et | CH | OMe | OMe |
| 1-71 | H | 5-Ph | CH | OMe | OMe |
| 1-72 | H | 5-Ph(4-Cl) | CH | OMe | OMe |
| 1-73 | H | 5-Ph(4-Me) | CH | OMe | OMe |
| 1-74 | H | 5-Ph(4-OMe) | CH | OMe | OMe |
| 1-75 | H | 5-NO2 | CH | OMe | OMe |
| 1-76 | H | 5-NH2 | CH | OMe | OMe |
| 1-77 | H | 5-NHMe | CH | OMe | OMe |
| 1-78 | H | 5-NMe2 | CH | OMe | OMe |
| 1-79 | H | 5-CN | CH | OMe | OMe |
| 1-80 | H | 4-F | CH | OMe | OMe |
| 1-81 | H | 4-C1 | CH | OMe | OMe |
| 1-82 | H | 4-Me | CH | OMe | OMe |
| 1-83 | H | 4-CF3 | CH | OMe | OMe |
| 1-84 | H | 4-OMe | CH | OMe | OMe |
| 1-85 | H | 4-CO2Et | CH | OMe | OMe |
| 1-86 | H | 4-COPh | CH | OMe | OMe |
| 1-87 | H | 3-Me | CH | OMe | OMe |
| 1-88 | H | 3-Cl | CH | OMe | OMe |
| 1-89 | H | 4,5-Cl2 | CH | OMe | OMe |
| 1-90 | H | 4,5-Me2 | CH | OMe | OMe |
| 1-91 | H | 4,5-(OMe)2 | CH | OMe | OMe |
| 1-92 | H | 4-CF3,6-Br | CH | OMe | OMe |
·· ···♦ • ·
3ο ( Tabulka 39)
| 1 učenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ůt20) |
| 1-93 | H | 4-CF3,6-Cl | CH | OMe | OMe | |
| 1-94 | H | 4,5,6-F3 | CH | OMe | OMe | |
| 1-95 | H | 6-Me | N | OMe | OMe | |
| 1-96 | H | 6-C1 | N | OMe | OMe | |
| 1-97 | H | • 5-F | N | OMe | OMe | |
| 1-98 | H | 5-Cl | N | OMe | OMe | |
| 1-99 | H | 5-Br | N | OMe | OMe | |
| 1-100 | H | 5-Me | N | OMe | OMe | |
| 1-101 | H | 5-CF3 | N | OMe | OMe | |
| 1-102 | H | 5-OMe | N | OMe | OMe | |
| 1-103 | H | 5-OEt | N | OMe | OMe | |
| 1-104 | H | 5-OPr | N | OMe | OMe | |
| 1-105 | H | 5-OCF3 | N | OMe | OMe | |
| 1-106 | H | 5-OCH2CH=CH2 | N | OMe | OMe | |
| 1-107 | H | 5-OCH2C=CH | N | OMe | OMe | |
| 1-108 | H | 5-OPh | N | OMe | OMe | |
| 1-109 | H | 5-SMe | N | OMe | OMe | |
| 1-110 | H | 5-COPh | N | OMe | OMe | |
| 1-111 | H | 5-CO2Et | N | OMe | OMe | |
| 1-112 | H | 5-Ph | N | OMe | OMe | |
| 1-113 | H | 5-Ph(4-Cl) | N | OMe | OMe | |
| 1-114 | H | 5-Ph(4-Me) | N | OMe | OMe | |
| 1-115 | H | 5-Ph(4-OMe) | N | OMe | OMe | |
| 1-116 | H | 5-NO2 | N | OMe | OMe | |
| 1-117 | H | 5-NH2 | N | OMe | OMe | |
| 1-118 | H | 5-NHMe | N | OMe | OMe | |
| 1-119 | H | 5-NMe2 | N | OMe | OMe | |
| 1-120 | H | 5-CN | N | OMe | OMe | |
| 1-121 | H | 4-F | N | OMe | OMe | |
| 1-122 | H | 4-C1 | N | OMe | OMe | |
| 1-123 | H | 4-Me | N | OMe | OMe | |
| 1-124 | H | 4-CF3 | N | OMe | OMe | |
| 1-125 | H | 4-OMe | N | OMe | OMe |
• *999 ( Tabulka 40 )
| 1 ~ sloučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ri ™ (no20) | |
| 1-126 | H | 4-NO2 | N | OMe | OMe | ||
| 1-127 | H | 4-CO2Et | N | OMe | OMe | ||
| 1-128 | H | 4-COPh | N | OMe | OMe | ||
| 1-129 | H | 3-Me | N | OMe | OMe | ||
| 1-130 | H | . 3-C1 | N | OMe | OMe | ||
| 1-131 | H | 4,5-Cl2 | N | OMe | OMe | ||
| 1-132 | H | 4,5-Me2 | N | OMe | OMe | ||
| 1-133 | H | 4,5-(OMe)2 | N | OMe | OMe | ||
| 1-134 | H | 4-CF3,6-Br | N | OMe | OMe | ||
| 1-135 | H | 4-CFs,6-Cl | N | OMe | OMe | ||
| 1-136 | H | 4,5,6-Fs | N | OMe | OMe | ||
| 1-137 | Me | 6-Me | CH | OMe | OMe | ||
| 1-138 | Me | 6-C1 | CH | OMe | OMe | ||
| 1-139 | Me | 6-F | CH | OMe | OMe | ||
| 1-140 | Me | 5-C1 | CH | OMe | OMe | ||
| 1-141 | Me | 5-Br | CH | OMe | OMe | ||
| 1-142 | Me | 5-Me | CH | OMe | OMe | ||
| 1-143 | Me | 5-Bu-t | CH | OMe | OMe | ||
| 1-144 | Me | 5-CF8 | CH | OMe | OMe | ||
| 1-145 | Me | 5-OMe | CH | OMe | OMe | ||
| 1-146 | Me | 5-COPh | CH | OMe | OMe | ||
| 1-147 | Me | 5-Ph | CH | OMe | OMe | ||
| 1-148 | Me | 5-NH2 | CH | OMe | OMe | ||
| 1-149 | Me | 5-NMe2 | CH | OMe | OMe | ||
| 1-150 | Me | 5-CN | CH | OMe | OMe | ||
| 1-151 | Me | 4-F | CH | OMe | OMe | ||
| 1-152 | Me | 4-C1 | CH | OMe | OMe | ||
| 1-153 | Me | 4-Me | CH | OMe | OMe | ||
| 1-154 | Me | 4-CF3 | CH | OMe | OMe | ||
| 1-155 | Me | 4-OMe | CH | OMe | OMe | ||
| 1-156 | Me | 4-.COPh | CH | OMe | OMe | ||
| 1-157 | Me | 4,5-Cl2 | CH | OMe | OMe | ||
| 1-158 | Me | 4,5-Me2 | CH | OMe | OMe |
4 ♦ 4 • · ···· •
• 4
444 (Tabulka 41 )
| 1 oučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo |
| 1-159 | Me | 4,5-(OMe)2 | CH | OMe | OMe | |
| 1-160 | Me | 6-Me | N | OMe | OMe | |
| 1-161 | Me | 6-C1 | N | OMe | OMe | |
| 1-162 | Me | 5-F | N | OMe | OMe | |
| 1-163 | Me | 5-C1 | N | OMe | OMe | |
| 1-164 | Me | 5-Br | N | OMe | OMe | |
| 1-165 | Me | 5-Me | N | OMe | OMe | 180-183 |
| 1-166 | Me | 5-Et | N | OMe | OMe | |
| 1-167 | Me | 5-Pr | N | OMe | OMe | |
| 1-168 | Me · | 5-Pr-i | N | OMe | OMe | |
| 1-169 | Me | 5-Bu-t | N | OMe | OMe | |
| 1-170 | Me | 5-CH=CH2 | N | OMe | OMe | |
| 1-171 | Me | 5-C = CBu | N | OMe | OMe | |
| 1-172 | Me | 5-CF3 | N | OMe | OMe | |
| 1-173 | Me | 5-OMe | N | OMe | OMe | |
| 1-174 | Me | 5-SMe | N | OMe | OMe | |
| 1-175 | Me | 5-COPh | N | OMe | OMe | |
| 1-176 | Me | 5-Ph | N | OMe | OMe | |
| 1-177 | Me | 5-NH2 | N | OMe | OMe | |
| 1-178 | Me | 5-NMe2 | N | OMe | OMe | |
| 1-179 | Me | 5-CN | N | OMe | OMe | |
| 1-180 | Me | 4-F | N | OMe | OMe | |
| 1-181 | Me | 4-C1 | N | OMe | OMe | |
| 1-182 | Me | 4-Me | N | OMe | OMe | |
| 1-183 | Me | 4-CF3 | N | OMe | OMe | |
| 1-184 | Me | 4-OMe | N | OMe | OMe | |
| 1-185 | Me | 4-OEt | N | OMe | OMe | |
| 1-186 | Me | 4-OPr | N | OMe | OMe | |
| 1-187 | Me | 4-CO2Et | N | OMe | OMe | |
| 1-188 | Me | 4-COPh | N | OMe | OMe | |
| 1-189 | Me | 4,5-Cl2 | N | OMe | OMe | |
| 1-190 | Me | 4,6-Me2 | N | OMe | OMe | |
| 1-191 | Me | 4,5-Me2 | N | OMe | OMe |
• · *·· · (Tabulka 42 )
| r~~ oučenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo Ti20) |
| 1-192 | Me | 4,5-(OMe)2 | N | OMe | OMe | |
| 1-193 | cf3 | 5-F | CH | OMe | OMe | 158-160 |
| 1-194 | cf3 | 5-C1 | CH | OMe | OMe | 150-151 |
| 1-195 | cf3 | 5-Br | CH | OMe | OMe | |
| 1-196 | cf3 | 5-Me | CH | OMe | OMe | 144-147 |
| 1-197 | cf3 | 5-CF3 | CH | OMe | OMe | 168-171 |
| 1-198 | cf3 | 5-OMe | CH | OMe | OMe | |
| 1-199 | cf3 | 5-OEt | CH | OMe | OMe | 122-125 |
| 1-200 | cf3 | 5-OPr | CH | OMe | OMe | |
| 1-201 | cf3 | 5-NMe2 | CH | OMe | OMe | |
| 1-202 | cf3 | 5-CN | CH | OMe | OMe | |
| 1-203 | cf3 | 4-F | CH | OMe | OMe | |
| 1-204 | cf3 | 4-C1 | CH | OMe | OMe | |
| 1-205 | cf3 | 4-Me | CH | OMe | OMe | |
| 1-206 | cf3 | 4,5-(OMe)2 | CH | OMe | OMe | |
| 1-207 | cf3 | 5-F | N | OMe | OMe | 202-205 |
| 1-208 | cf3 | 5-CI | N | OMe | OMe | |
| 1-209 | cf3 | 5-Br | N | OMe | OMe | |
| 1-210 | cf3 | 5-Me | N | OMe | OMe | 195-198 |
| 1-211 | cf3 | 5-Et | N | OMe | OMe | 182-185 |
| 1-212 | cf3 | 5-Pr | N | OMe | OMe | 141-144 |
| 1-213 | cf3 | 5-Pr-i | N | OMe | OMe | 193-196 |
| 1-214 | cf3 | 5-Bu-t | N | OMe | OMe | 215-218 |
| 1-215 | cf3 | 5-CF3 | N | OMe | OMe | |
| 1-216 | cf3 | 5-OMe | N | OMe | OMe | 183-185 |
| 1-217 | cf3 | 5-OEt | N | OMe | OMe | |
| 1-218 | cf3 | 5-OPr | N | OMe | OMe | |
| 1-219 | cf3 | 5-OCF3 | N | OMe | OMe | 188-191 |
| 1-220 | cf3 | 5-SMe | N | OMe | OMe | |
| 1-221 | cf3 | 5-NHMe | N | OMe | OMe | |
| 1-222 | cf3 | 5-NMe2 | N | OMe | OMe | |
| 1-223 | cf3 | 5-CN | N | OMe | OMe | |
| 1-224 | cf3 | 5-CO2Me | N | OMe | OMe | 186-189 |
• ♦ ··· · • · • · • · ·· (Tábulka43 )
m.p. (°C) nebo
| 1-225 | cf3 | 5-1 | N | OMe | OMe | 169-172 |
| 1-226 | cf3 | 4-F | N | OMe | OMe | |
| 1-227 | cf3 | 4-Cl | N | OMe | OMe | |
| 1-228 | cf3 | 6-Me | N | OMe | OMe | |
| 1-229 | cf3 | 4,5-(OMe)2 | N | OMe | OMe | |
| 1-230 | Et | 5-F | CH | OMe | OMe | |
| 1-231 | Et | 5-C1 | CH | OMe | OMe | |
| 1-232 | Et | 5-Me | CH | OMe | OMe | |
| 1-233 | Et | 5-CF3 | CH | OMe | OMe | |
| 1-234 | Et | 5-OMe | CH | OMe | OMe | |
| 1-235 | Et | 5-CN | CH | OMe | OMe | |
| 1-236 | Et | 4-F | CH | OMe | OMe | |
| 1-237 | Et | 4-Cl | CH | OMe | OMe | |
| 1-238 | Et | 4-Me | CH | OMe | OMe | |
| 1-239 | Et | 4,5-(OMe)2 | CH | OMe | OMe | |
| 1-240 | Et | 5-F | N | OMe | OMe | |
| 1-241 | Et | 5-C1 | N | OMe | OMe | |
| 1-242 | Et | 5-Me | N | OMe | OMe | |
| 1-243 | . Et | 5-CF3 | N | OMe | OMe | |
| 1-244 | Et | 5-OMe | N | OMe | OMe | |
| 1-245 | Et | 5-CN | N | OMe | OMe | |
| 1-246 | Et | 4-F | N | OMe | .OMe | |
| 1-247 | Et | 4-C1 | N | OMe | OMe | |
| 1-248 | Et | 4-Me | N | OMe | OMe | |
| 1-249 | Et | 4,5-(OMe)2 | N | OMe | OMe | |
| 1-250 | Pr | 5-C1 | N | OMe | OMe | 137-140 |
| 1-251 | Pr-i | 5-C1 | N | OMe | OMe | 149-152 |
| 1-252 | Pr-c | 5-C1 | N | OMe | OMe | 181-184 |
| 1-253 | CH,OMe | 5-C1 | N | OMe | OMe | |
| 1-254 | Ph | 5-C1 | N | OMe | OMe | 176-179 |
| 1-255 | Ph | 5-Br | N | OMe | OMe | |
| 1-256 | Ph(4-Cl) | 5-C1 | N | OMe | OMe | |
| 1-257 | Ph(4-Me) | 5-C1 | N | OMe | OMe |
• 0
0 00
Λ (Tabulka 44:)
| 1 učenina č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ri (nD 20) |
| 1-258 | Ph(4-OMe) 5-C1 | N | OMe | OMe | ||
| 1-259 | Bn | 5-C1 | N | OMe | OMe | |
| 1-260 | CF2C1 | 5-Me | N | OMe | OMe | |
| 1-261 | cf2ci | 5-C1 | N | OMe | OMe | |
| 1-262 | cf2ci | 5-Br | N | OMe | OMe | |
| 1-263 | cf2ci | 5-OMe | N | OMe | OMe | |
| 1-264 | ch2ci | 5-Me | N | OMe | OMe | |
| 1-265 | ch2ci | 5-C1 | N | OMe | OMe | |
| 1-266 | ch2ci | 5-Br | N | OMe | OMe | |
| 1-267 | ch2ci | 5-OMe | N | OMe | OMe | |
| 1-268 | c2f5 | 5-Me | N | OMe | OMe | |
| 1-269 | c2fs | 5-C1 | N | OMe | OMe | |
| 1-270 | c2f5 | 5-Br | N | OMe | OMe | |
| 1-271 | C2F5 | 5-OMe | N | OMe | OMe | |
| 1-272 | Ph(4-Cl) | 5-OMe | CH | OMe | OMe | 187-200 |
| 1-273 | CH2OMe | 5-C1 | N | OMe | OMe | 183-186 |
| 1-274 | cf3 | 5-Me | N | OMe | OEt | |
| 1-275 | cf3 | 5-C1 | N | OMe | OEt | |
| 1-276 | cf3 | 5-Br | N | OMe | OEt | |
| 1-277 | cf2ci | 5-Cl | N | OMe | OEt | |
| 1-278 | cf2ci | 5-Br | N | OMe | OEt | |
| 1-279 | cf2ci | 5-Me | N | OMe | OEt | |
| 1-280 | ch2ci | 5-C1 | N | OMe | OEt | |
| 1-281 | ch2ci | 5-Br | N | OMe | OEt | |
| 1-282 | ch2ci | 5-Me | N | OMe | OEt | |
| 1-283 | c2f5 | 5-C1 | N | OMe | OEt | |
| 1-284 | c2f5 | 5-Br | N | OMe | OEt | |
| 1-285 | c2f5 | 5-Me | N | OMe | OEt | |
| 1-286 | Me | 5-F | CH | OEt | OEt | |
| 1-287 | Me | 5-C1 | CH | OEt | OEt | |
| 1-288 | Me | 5-Br | CH | OEt | OEt | |
| 1-289 | Me | 5-Me | CH | OEt | OEt | |
| 1-290 | Me | 5-CF3 | CH | OEt | OEt |
(Tabulka 45 ) ·♦ · ·Φ« ·
| 1 | m.p. (°C) | ||||||
| sloučenina | X | Yn | A | R1 | R2 | nebo | |
| v | RI | ||||||
| c. | (¾20) | ||||||
| 1-291 | Me | 5-F | N | OEt | OEt | ||
| 1-292 | Me | 5-CI | N | OEt | OEt | ||
| 1-293 | Me | 5-Br | N | OEt | OEt | ||
| 1-294 | Me | 5-Me | N | OEt | OEt | ||
| 1-295 | Me | 5-CF3 | N | OEt | OEt | ||
| 1-296 | cf3 | 5-F | CH | OEt | OEt | ||
| 1-297 | cf3 | 5-C1 | CH | OEt | OEt | ||
| 1-298 | cf3 | 5-Br | CH | OEt | OEt | ||
| 1-299 | cf3 | 5-Me | CH | OEt | OEt | ||
| 1-300 | cf3 | 5-CF3 | CH | OEt | OEt | ||
| 1-301 | cf3 | 5-OMe | N | OEt | OEt | 159-161 | |
| 1-302 | cf3 | 5-C1 | N | OEt | OEt | 194-197 | |
| 1-303 | cf3 | 5-Br | N | OEt | OEt | 191-194 | |
| 1-304 | cf3 | 5-Me | N | OEt | OEt | 201-204 | |
| 1-305 | cf3 | 5-CF3 | N | OEt | OEt | ||
| 1-306 | Ph | H | N | OEt | OEt | ||
| 1-307 | Ph(4-Cl) | H | N | OEt | OEt | ||
| 1-308 | Ph(4-Me) | H | N | OEt | OEt | ||
| 1-309 | Ph(4-OMe) H | N | OEt | OEt | |||
| 1-310 | Ph | 5-C1 | N | OEt | OEt | ||
| 1-311 | Ph(4-Cl) | 5-C1 | N | OEt | OEt | ||
| 1-312 | Ph(4-Me) | 5-C1 | N | OEt | OEt | ||
| 1-313 | Ph(4-OMe) 5-C1 | N | OEt | OEt | |||
| 1-314 | Ph | 5-Br | N | OEt | OEt | ||
| 1-315 | Ph(4-Cl) | 5-Br | N | OEt | OEt | ||
| 1-316 | Ph(4-Me) | 5-Br | N | OEt | OEt | ||
| 1-317 | Ph(4-0Me) 5-Br | N | OEt | OEt | |||
| 1-318 | H | H | CH | OPr | OPr | ||
| 1-319 | Me | 5-C1 | N | OPr | OPr | ||
| 1-320 | Me | 5-Br | N | OPr | OPr | ||
| 1-321 | Me | 5-Me | N | OPr | OPr | ||
| 1-322 | cf3 | 5-C1 | N | OPr | OPr | 150-153 | |
| 1-323 | cf3 | 5-Br | N | OPr | OPr |
• 4 ς>
(Tabulka 46 ) • · · 4
44 44 4 4 sloučenina
r.
A R1
X
Yn
R2
m.p. (°C) nebo
RI
| v. | (nD zu) | |||||
| 1-324 | cf3 | 5-Me | N | OPr | OPr | |
| 1-325 | . H | H | CH | OPr-i | OPr-i | |
| 1-326 | Me | 5-C1 | CH | OPr-i | OPr-i | |
| 1-327 | Me | 5-Me | CH | OPr-i | OPr-i | |
| 1-328 | Me | 5-C1 | N | OPr-i | OPr-i | |
| 1-329 | Me | 5-Br | N | OPr-i ’ | OPr-i | |
| 1-330 | Me | 5-Me | N | OPr-i | OPr-i | |
| 1-331 | cf3 | 5-C1 | N | OPr-i | OPr-i | 198-201 |
| 1-332 | cf3 | 5-Br | N | OPr-i | OPr-i | |
| 1-333 | cf3 | 5-Me | N | OPr-i | OPr-i | |
| 1-334 | Me | 5-C1 | N | OCH2CH=CH2 | OCH2CH=CH2 | |
| 1-335 | Me | 5-Br | N | och2ch=ch2 | OCH2CH=CH2 | |
| 1-336 | Me | 5-Me | N | och2ch=ch2 | och2ch=ch2 | |
| 1-337 | cf3 | 5-C1 | • N | och2ch=ch2 | och2ch=ch. | 121-124 |
| 1-338 | cf3 | 5-Br | N | och2ch=ch2 | och2ch=ch2 | |
| 1-339 | cf3 | 5-Me | N | och2ch=ch2 | och2ch=ch2 | |
| 1-340 | Me | 5-C1 | N | och2c=ch | och2c=ch | |
| 1-341 | Me | 5-Br | N | OCH2C=ch | och2c=ch | |
| 1-342 | Me | 5-Me | N | och2c=ch | och2c=ch | |
| 1-343 | cf3 | 5-C1 | N | 0CH2C=CH | och2c=ch | |
| 1-344 | cf3 | 5-Br | N | OCH2C = CH | OCH2CsCH | |
| 1-345 | cf3 | 5-Me | N | OCH2CSCH | OCH2CsCH | |
| 1-346 | Me | 5-C1 | CH | och2cn | och2cn | |
| 1-347 | Me | 5-Me | CH | och2cn | och2cn | |
| 1-348 | Me | 5-C1 | N | och2cn | och2cn | |
| 1-349 | Me | 5-Br | N | och2cn | och2cn | |
| 1-350 | Me | 5-Me | N | och2cn | och2cn | |
| 1-351 | cf3 | 5-C1 | N | och2cn | och2cn | |
| 1-352 | cf3 | 5-Br | N | och2cn | och2cn | |
| 1-353 | cf3 | 5-Me | N | och2cn | och2cn | |
| 1-354 | Me | 5-C1 | CH | 0CH2CH20Me | OCH2CH2OMe | |
| 1-355 | Me | 5-Me | CH | OCH2CH2OMe | OCH2CH2OMe | |
| 1-356 | H | 5-Br | N | OCH2CH2OMe | OCH,CH2OMe |
(Tabulka 47 )
| ·· | • | ·· ··»« | 9 9 |
| • 9 | • | • · · | 9 9 9 |
| • · | • r | • · « | • · |
| • 9 | 99 99 | ♦ · · · | 9 9 9 |
| 9 9 | 9 | • · 9 | 9 9 |
| 9 9 | • | 9 9 9 | 9 9 · |
| L . ucemna č. | L X | Yn | A | R1 | R2 | m.p. (° nebo ton20) |
| 1-357 | Me | 5-C1 | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-358 | Me | 5-Br | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-359 | Me | 5-Me | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-360 | cf3 | 5-C1 | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-361 | cf3 | 5-Br | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-362 | cf3 | 5-Me | N | OCH2CH2OMe | OCH2CH2OMe | |
| 1-363 | H | 5-Br | N | OCH2Pr-c | OCH2Pr-c | |
| 1-364 | Me | 5-C1 | N | OCH2Pr-c | OCH2Pr-c | |
| 1-365 | Me | 5-Br | N | OCH2Pr-c | OCH2Pr-c | |
| 1-366 | Me | 5-Me | N | OCH2Pr-c | OCH2Pr-c | |
| 1-367 | cf3 | 5-C1 | N | OCH2Pr-c | OCH2Pr-c | |
| 1-368 | cf3 | 5-Br | N | OCH2Pr-c | OCH2Pr-c | |
| 1-369 | cf3 | 5-Me | N | OCH2Pr-c | OCH2Pr-c | |
| 1-370 | H | H | CH | OBn | OBn | |
| 1-371 | H | H | N | OBn | OBn | |
| 1-372 | H | H | N | OBn(4-Cl) | OBn(4-Cl) | |
| 1-373 | H | H | N | OBn(4-Me) | OBn(4-Me) | |
| 1-374 | H | H | N | OBn(4-OMe) | OBn(4-OMe) | |
| 1-375 | H | H | CH | OMe | OPh | |
| 1-376 | H | H | N | OMe | OPh | |
| 1-377 | H | H | N | OMe | 0Ph(4-Cl) | |
| 1-378 | H | H | N | OMe | OPh(4-Me) | |
| 1-379 | H | H | N | OMe | OPh(4-OMe) | |
| 1-380 | H | H | CH | OMe | ochf2 | |
| 1-381 | H | H | N | OMe | ochf2 | |
| 1-382 | Me | 5-C1 | CH | OMe | H | |
| 1-383 | Me | 5-Me | CH | OMe | H | |
| 1-384 | Me | 5-CFj | CH | OMe | H | |
| 1-385 | Me | 5-OMe | CH | OMe | H | |
| .1-386 | cf3 | 5-C1 | CH | OMe | H | 125-128 |
| 1-387 | cf3 | 5-Me | CH | OMe | H | 130-133 |
| 1-388 | cf3 | 5-CF3 | CH | OMe | H | |
| 1-389 | cf3 | 5-OMe | CH | OMe | H | 153-156 |
·« ΜΙ» • f ···« ( Tabulka 48 )
m.p. (°C) nebo RI _
| 1-390 | cf3 | 5-C1 | CH | OEt | H | |
| 1-391 | cf3 | 5-Me | CH | OEt | H | 125-127 |
| 1-392 | cf3 | 5-OMe | CH | OEt | H | |
| 1-393 | Me | 5-C1 | CH | OMe | Me | |
| 1-394 | Me | 5-Me | CH | OMe | Me | |
| 1-395 | Me | 5-CF3 | CH | OMe | Me | |
| 1-396 | cf3 | 5-C1 | CH | OMe | Me | |
| 1-397 | cf3 | 5-Me | CH | OMe | Me | |
| 1-398 | cf3 | 5-OMe | CH | OMe | Me | |
| 1-399 | Me | 5-C1 | N | OMe | Me | |
| 1-400 | Me | 5-Me | N | OMe | Me | |
| 1-401 | Me | 5-CF3 | N | OMe | Me | |
| 1-402 | cf3 | 5-C1 | N | OMe | Me | |
| 1-403 | cf3 | 5-Me | N | OMe | Me | 192-195 |
| 1-404 | cf3 | 5-OMe | N | OMe | Me | |
| 1-405 | cf3 | 5-C1 | N | OMe | Pr | |
| 1-406 | cf3 | 5-Br | N | OMe | Pr | |
| 1-407 | cf3 | 5-Me | N | OMe | Pr | 149-152 |
| 1-408 | cf3 | 5-C1 | N | OMe | Pr-c | |
| 1-409 | cf3 | 5-Br | N | OMe | Pr-c | |
| 1-410 | cf3 | 5-Me | N | OMe | Pr-c | 103-106 |
| 1-411 | cf3 | 5-C1 | N | OEt | Pr-c | |
| 1-412 | cf3 | 5-Me | N | OEt | Pr-c | |
| 1-413 | cf3 | 5-CF3 | N | OEt | Pr-c | |
| 1-414 | Me | 5-C1 | CH | OEt | Me | |
| 1-415 | Me | 5-Me | CH | OEt | Me | |
| 1-416 | Me | 5-CFs | CH | OEt | Me | |
| 1-417 | Me | 5-OMe | CH | OEt | Me | |
| 1-418 | cf3 | 5-C1 | CH | OEt | Me | |
| 1-419 | cf3 | 5-Me | CH | OEt | Me | |
| 1-420 | cf3 | 5-OMe | CH | OEt | Me | 136-139 |
| 1-421 | Me | 5-Cl | N | OEt | Me | |
| 1-422 | Me | 5-Br | N | OEt | Me |
Co (Tabulka 49 )
| ♦ · | «··· | |
| · | « | • |
| • | 9 | 9 |
| • · | • | ♦ |
| • | • | • |
| • 4 | 4 |
| <-------------------- sloučenina | X | Yn | A | R1 | R2 | m.p. (°C) nebo Tne20) | |
| č. | |||||||
| 1-423 | Me | 5-Me | N | OEt | Me | ||
| 1-424 | Me | 5-CF3 | N | OEt | Me | ||
| 1-425 | CFg | 5-C1 | N | OEt | Me | ||
| 1-426 | cf3 | 5-Br | N | OEt | Me | ||
| 1-427 | cf3 | 5-Me | N | OEt | Me | ||
| 1-428 | cf3 | 5-C1 | CH | OCH2CH=CH2 | Me | ||
| 1-429 | cf3 | 5-Me | CH | OCH2CH=CH2 | Me | ||
| 1-430 | cf3 | 5-OMe | CH | och2ch=ch2 | Me | ||
| 1-431 | cf3 | 5-C1 | N | och2ch=ch2 | Me | ||
| 1-432 | cf3 | 5-Me | N | och2ch=ch2 | Me | 175-178 | |
| 1-433 | cf3 | 5-OMe | N | och2ch=ch2 | Me | ||
| 1-434 | cf3 | 5-Me | CH | SMe | Me | ||
| 1-435 | cf3 | 5-CI | CH | SMe | Me | ||
| 1-436 | cf3 | 5-Me | N | SMe | Me | 196-199 | |
| 1-437 | cf3 | 5-C1 | N | SMe | Me | 157-160 | |
| 1-438 | cf3 | 5-C1 | N | OMe | Et | ||
| 1-439 | cf3 | 5-Br | N | OMe | Et | ||
| 1-440 | cf3 | 5-Me | N | OMe | Et | ||
| 1-441 | cf3 | 5-C1 | N | OEt | Et | ||
| 1-442 | cf3 | 5-Br | N | OEt | Et | ||
| 1-443 | cf3 | 5-Me | N | OEt | Et | ||
| 1-444 | Me | 5-C1 | N | SMe | SMe | ||
| 1-445 | Me | 5-Br | N | SMe | SMe | ||
| 1-446 | Me | 5-Me | N | SMe | SMe | ||
| 1-447 | cf3 | 5-C1 | N | SMe | SMe | ||
| 1-448 | cf3 | 5-Br | N | SMe | SMe | ||
| 1-449 | cf3 | 5-Me | N | SMe | SMe | ||
| 1-450 | Me | 5-C1 | N | OMe | SMe | ||
| 1-451 | Me | 5-Br | N | OMe | SMe | ||
| 1-452 | cf3 | 5-C1 | N | OMe | SMe | ||
| 1-453 | cf3 | 5-Br | N | OMe | SMe | ||
| 1-454 | cf3 | 5-Me | N | OMe | SMe | ||
| 1-455 | Me | 5-Me | N | OMe | Ph |
Μ (Tabulka 50 )
| ·« | φ | ΦΦ | φφφφ | »· | « | |||
| • | • | φ | φ | φ | φ | «1 | φ | φ φ |
| • | • | φ φ | φ | φ | φ | φ | φ | φ |
| • | φ | φφφφ | φ φ | φ | φ | φ φ | φ | φ |
| • · | φ | φ | φ | • | φ | φ | φ | |
| ΦΦ | φ | ΦΦ | φ | ΦΦ | ·Φ· |
| 1 oučenina Č. | X | Yn | A | R1 | R2 | m.p. (°C) nebo ď20) |
| 1-456 | cf3 | 5-Me | N | OMe | Ph | 219-222 |
| 1-457 | Me | H | CH | Cl | Cl | |
| 1-458 | Me | 4,5-Cl2 | CH | Cl | Cl | |
| 1-459 | Me | H | N | Cl | Cl | |
| 1-460 | Me | H | CH | Cl | Me | |
| 1-461 | Me | 5-C1 | N | NMe2 | NMe2 | |
| 1-462 | cf3 | 5-C1 | N | NMe2 | NMe2 | 219-222 |
| 1-463 | H | H | CH | OMe | NMe2 | |
| 1-464 | H | H | CBr | OMe | OMe | |
| 1-465 | H | H | CMe | Cl | Cl | |
| 1-466 | Me | 5-Me | COMe | H | H | |
| 1-467 | Me | 5-C1 | COMe | H | H | |
| 1-468 | Me | 5-C1 | CH | Me | Me | |
| 1-469 | Me | 5-CF3 | CH | Me | Me | |
| 1-470 | Me | 5-Cl | CH | Me | cf3 | |
| 1-471 | Me | 5-Me | CH | Me | Et | |
| 1-472 | Me | 5-C1 | CH | Me | Et | |
| 1-473 | cf3 | 5-Me | CH | Me | Et | |
| 1-474 | CFS | 5-C1 | CH | Me | Et | |
| 1-475 | Me | 5-Me | CH | Me | Pr-c | |
| 1-476 | Me | 5-C1 | CH | Me | Pr-c | |
| 1-477 | cf3 | 5-Me | CH | Me | Pr-c | |
| 1-478 | cf3 | 5-C1 | CH | Me | Pr-c | |
| 1-479 | cf3 | 5-C1 | CH | C=CMe | Me | |
| 1-480 | cf3 | 5-C1 | N | C = CMe | Me | |
| 1-481 | cf3 | 5-C1 | CH | CH=CH2 | Me | |
| 1-482 | cf3 | 5-C1 | N | ch=ch3 | Me | |
| 1-483 | Me | 5-C1 | CH | CHO | Me | |
| 1-484 | Me | 5-C1 | N | CHO | Me | |
| 1-485 | Me | 5-CI | CH | COMe | Me | |
| 1-486 | Me | 5-Cl | N | COMe | Me | |
| 1-487 | Me | 5-C1 | CH | CH2OMe | Me | |
| 1-488 1 | Me | 5-Me | CH | CHjOMe | Me |
(Tabulka 51 ) i
sloučenina
1-489
1-490
1-491
1-492
1-493
1-494
1-495
CL
| X | Yn | A | R1 | R2 | m.p. (°C) nebo |
| Me | H | CH | CN | CN | |
| Me | H | CH | CN | Me | |
| Me | H | N | CN | CN | |
| Me | H | N | CN | Me | |
| Me | H | CH | SO2Me | SO2Me | |
| Me | H | N | SO2Me | SO2Me | |
| Me | H | CH | SO2Me | Me |
» • · · · • · • ·
( Tabulka 52 )
Rl
| mčenina v c. | Yn | A | R1 | R2 | m.p. (°c) nebo |
| 2-1 | 3-Me | CH | OMe | OMe | |
| 2-2 | 3-Cl | CH | OMe | OMe | |
| 2-3 | 4-F | CH | OMe | OMe | 194-196 |
| 2-4 | 4-C1 | CH | OMe | OMe | 188-190 |
| 2-5 | 4-Br | CH | OMe | OMe | 191-194 |
| 2-6 | 4-Me | CH | OMe | OMe | 158-161 |
| 2-7 | 4-Bu-t | CH | OMe | OMe | |
| 2-8 | 4-CF3 | CH | OMe | OMe | 178-180 |
| 2-9 | 4-OMe | CH | OMe | OMe | 189-190 |
| 2-10 | 4-OEt | CH | OMe | OMe | 178-180 |
| .2-11 | 4-OPr | CH | OMe | OMe | |
| 2-12 | 4-OCFs | CH | OMe | OMe | 144-147 |
| 2-13 | 4-OCH2CH=CH2 | CH | OMe | OMe | |
| 2-14 | 4-OCH2CsCH | CH | OMe | OMe | |
| 2-15 | 4-OPh | CH | OMe | OMe | |
| 2-16 | 4-OPh(4-Cl) | CH | OMe | OMe | |
| 2-17 | 4-OPh(4-Me) | CH | OMe | OMe | |
| 2-18 | 4-OPh(4-OMe) | CH | OMe | OMe | |
| 2-19 | 4-SMe | CH | OMe | OMe | |
| 2-20 | 4-CH2OMe | CH | OMe | OMe | |
| 2-21 | 4-COMe | CH | OMe | OMe | |
| 2-22 | 4-COPh | CH | OMe | OMe | |
| 2-23 | 4-CO2Et | CH | OMe | OMe | |
| 2-24 | 4-Ph | CH | OMe | OMe |
• · · · • ·
(,ί (Tabulka53 )
| 1 >učenina č. | Yn | A | R1 | R2 | m.p. (°Č) nebo |
| 2-25 | 4-Ph(4-Cl) | CH | OMe | OMe | |
| 2-26 | 4-Ph(4-Me) | CH | OMe | OMe | |
| 2-27 | 4-Ph(4-OMe) | CH | OMe | OMe | |
| 2-28 | 4-NO2 | CH | Ome | OMe | |
| 2-29 | 4-NH2 | CH | OMe | OMe | |
| 2-30 | 4-NHMe | CH | OMe | OMe | |
| 2-31 | 4-NMe2 | CH | OMe | OMe | |
| 2-32 | 4-CN | CH | OMe | OMe | 241-244 |
| 2-33 | 5-F | CH | OMe | OMe | |
| 2-34 | 5-C1 | CH | OMe | OMe | |
| 2-35 | 5-Me | CH | OMe | OMe | |
| 2-36 | 5-CF3 | CH | OMe | OMe | |
| 2-37 | 5-OMe | CH | OMe | OMe | |
| 2-38 | 5-CO2Me | CH | OMe | OMe | |
| 2-39 | 5-COPh | CH | OMe | OMe | |
| 2-40 | 6-Me | CH | OMe | OMe | 136-139 |
| 2-41 | 6-C1 | CH | OMe | OMe | |
| 2-42 | 4,5-Cl2 | CH | OMe | OMe | |
| 2-43 | 4,5-Me2 | CH | OMe | OMe | |
| 2-44 | 4,5-(OMe)2 | CH | OMe | OMe | |
| 2-45 | 4,6-Me2 | CH | OMe | OMe | 139-142 |
| 2-46 | 3-Br,5-CF3 | CH | OMe | OMe | |
| 2-47 | 3-Cl,5-CF3 | CH | OMe | OMe | |
| 2-48 | 3,4,5-Fg | CH | OMe | OMe | |
| 2-49 | H | N | OMe | OMe | 177-180 |
| 2-50 | 3-Me | N | OMe | OMe | |
| 2-51 | 3-C1 | N | OMe | - OMe | |
| 2-52 | 4-F | N | OMe | OMe | 184-187 |
| 2-53 | 4-C1 | N | OMe | OMe | 206-208 |
| 2-54 | 4-Br | N | OMe | OMe | |
| 2-55 | 4-1 | N | OMe | OMe | 218-221 |
(Tabulka 54)
| γ; sloučenina č. | 1 Yn | A | R1 | R2 | m.p. (°C) nebo (i°) | |
| 2-56 | 4-Me | N | OMe | OMe | 189-191 | |
| 2-57 | 4-Et | N | OMe | OMe | 146-149 | |
| 2-58 | 4-Pr | N | OMe | OMe | 170-173 | |
| 2-59 | 4-CF3 | N | OMe | OMe | ||
| 2-60 | 4-Bu-t | N | OMe | OMe | 118-121 | |
| 2-61 | 4-C = CBu-t | N | OMe | OMe | 117-120 | |
| 2-62 | 4-OMe | N | OMe | OMe | 197-199 | |
| 2-63 | 4-OEt | N | OMe | OMe | ||
| 2-64 | 4-OPr | N ' | OMe | OMe | ||
| 2-65 | 4-OCFg | N | OMe | OMe | 119-122 | |
| 2-66 | 4-OCH2CH=CH2 | N | OMe | OMe | ||
| 2-67 | 4-OCH2CsCH | N . | OMe | OMe | ||
| 2-68 | 4-OPh | N | OMe | OMe | ||
| 2-69 | 4-SMe | N | OMe | OMe | ||
| 2-70 | 4-COPh. | N | OMe | OMe | 221-224 | |
| 2-71 | 4-CO2Me | N | OMe | OMe | 289-292 | |
| 2-72 | 4-Ph | N | OMe | OMe | ||
| ,2-73 | 4-Ph(4-Cl) | N | OMe | OMe | ||
| 2-74 | 4-Ph(4-Me) | N | OMe | OMe | ||
| 2-75 | 4-Ph(4-OMe) | N | OMe | OMe | ||
| 2-76 | 4-NO2 | N | OMe | OMe | ||
| 2-77 | 4-NH2 | N | OMe | OMe | ||
| 2-78 | 4-NHMe | N | OMe | OMe | ||
| 2-79 | 4-NMe2 | N | OMe | OMe | 155-158 | |
| 2-80 | 4-CN | N ' | OMe | OMe | 189-201 | |
| 2-81 | 5-F | N | OMe | OMe | ||
| 2-82 | 5-C1 | N | OMe | OMe | ||
| 2-83 | 5-Me | N | . OMe | OMe | 151-154 | |
| 2-84 | 5-CF3 | N | OMe | OMe | ||
| 2-85 | 5-OMe | N | OMe | OMe | ||
| 2-86 | 5-NČ>2 | N | OMe | OMe |
• · 4 4 · 4444«4
444 44 4444
4444 44 ·44
4444444 4 4 44·
4 44 4 444 (Tabulka 55 )
| Γ“~ oučenina č. | Yn | A | R1 | R2 | m.p. (°C) nebo |
| 2-87 | 5-CO2Et | N | OMe | OMe | |
| 2-88 | 5-COPh | N | OMe | OMe | |
| 2-89 | 6-Me | N | OMe | OMe | |
| 2-90 | 6-Cl | N | OMe | OMe | |
| 2-91 | 4,5-Cl2 | N | OMe | OMe | |
| 2-92 | 4,5-Me2 | N | OMe | OMe | |
| 2-93 | 4,5-(OMe)z | N | OMe | OMe | |
| 2-94 | 3-Br,5-CF3 | N | OMe | OMe | |
| 2-95 | 3-Cl,5-CF3 | N | OMe | OMe | |
| 2-96 | 3,4,5-Fg | N | OMe | OMe | |
| 2-97 | 4-Me | N | OMe | OEt | 173-175 |
| 2-98 | 4-Cl | N | OMe | OEt | 130-132 |
| 2-99 | 4-Br | N | OMe | OEt | |
| 2-100 | H | CH | OEt | OEt | 92-95 |
| 2-101 | 4-F | CH | OEt | OEt | 131-134 |
| 2-102 | 4-C1 | CH | OEt | OEt | 147-149 |
| 2-103 | 4-Br | CH | OEt | OEt | |
| 2-104 | 4-Me | CH | OEt | OEt | 147-150 |
| 2-105 | 4-CF3 | CH | OEt | OEt | 134-137 |
| 2-106 | 4-F | N | OEt | OEt | |
| 2-107 | 4-Cl | N | OEt | OEt | |
| 2-108 | 4-Br | N | OEt | OEt | |
| 2-109 | 4-Me | N | OEt | OEt | |
| 2-110 | 4-CF3 | N | OEt | OEt | |
| 2-111 | 4-Cl | N | OPr | OPr | |
| 2-112 | 4-Cl | CH | OPr-i | OPr-i | |
| 2-113 | 4-Me | CH | OPr-i | OPr-i | |
| 2-114 | 4-Cl | N | OPr-i | OPr-i | |
| 2-115 | 4-Br | N | OPr-i | OPr-i | |
| 2-116 | 4-C1 | N | OCH2CH=CH2 | OCH2CH=CH2 | |
| 2-117 | 4-Br | N | OCH2CH=CH2 | OCH2CH=CH2 |
(Tabulka 56 ) j— sloučenina
«·· ······ · · « · « · · · · ♦ · ···· · · · · · • ······· · · · · · • · · ··♦ · · • · · · · · · · ·
m.p. (°C)
| 2-118 | 4-C1 | N | OCH2C=CH | OCH2C=CH |
| 2-119 | 4-Br | N | 0CH2CsCII | och2c=ch |
| 2-120 | 4-C1 | N | och2cn | och2cn |
| 2-121 | 4-Br | N | och2cn | och2cn |
| 2-122 | 4-Br | N | OCH2CH2OMe | OCH2CH2OMe |
| 2-123 | 4-C1 | N | OCH2CH2OMe | OCH2CH2OMe |
| 2-124 | 4-Br | N | 0CH2Pr-c | OCH2Pr-c |
| 2-125 | 4-C1 | N | OCH2Pr-c | OCH2Pr-c |
| 2-126 | H | CH | OBn | OBn |
| 2-127 | H | N | OBn | OBn |
| 2-128 | H | N | OBn(4-Cl) | OBn(4-Cl) |
| 2-129 | H | N | OBn(4-Me) | OBn(4-Me) |
| 2-130 | H | N | 0Bn(4-0Me) | OBn(4-OMe) |
| 2-131 | H | CH | OMe | OPh |
| 2-132 | H | N | OMe | OPh |
| 2-133 | H | N | OMe | OPh(4-Cl) |
| 2-134 | H | N | OMe | OPh(4-Me) |
| 2-135 | H | N | OMe | OPh(4-OMe) |
| 2-136 | H | CH | OMe | ochf2 |
| 2-137 | H | N | OMe | ochf2 |
| 2-138 | 4-C1 | CH | OMe | H |
| 2-139 | 4-Me | CH | OMe | H |
| 2-140 | 4-C1 | CH | OEt | H |
| 2-141 | 4-Me | CH | OEt | H |
| 2-142 | 4-C1 | CH | OMe | Me |
| 2-143 | 4-Me | CH | OMe | Me |
| 2-144 | 4-CF3 | CH | OMe | Me |
| 2-145 | 4-Cl | N | OMe | Me |
| 2-146 | 4-Me | N | OMe | Me |
| 2-147 | 4-C1 | N | OMe | Pr |
| 2-148 | 4-Me | N | OMe | Pr |
65-68
136-139
136-139
118-119
99-100
155-158
116-119 a
(Tabulka 57)
| 1 sloučenina v c. | Yn | A | R1 | R2 | m.p. (°C) nebo t) | |
| 2-149 | 4-C1 | N | OMe | Pr-c | ||
| 2-150 | 4-Br | N | OMe | Pr-c | ||
| 2-151 | 4-Me | N | OMe | Pr-c | 130133 | |
| 2-152 | 4-C1 | N | OEt | Pr-c | ||
| 2-153 | 4-Me | N | OEt | Pr-c | ||
| 2-154 | 4-C1 | N | OMe | Et | 109-112 | |
| 2-155 | 4-Br | N | OMe | Et | 113-116 | |
| 2-156 | 4-Me | N | OMe | Et | ||
| 2-157 | 4-C1 | N | OEt | Et | ||
| 2-158 | 4-Br | N | OEt | Et | ||
| 2-159 | 4-Me | N | OEt | Et | ||
| 2-160 | 4-Me | N | OPr | Me | 175-178 | |
| 2-161 | 4-C1 | N | OPr | Me | ||
| 2-162 | 4-Me | CH | Me | Et | 75-78 | |
| 2-163 | 4-C1 | CH | Me | Et | ||
| 2-164 | 4-Me | CH | Et | Et | 64-67 | |
| 2-165 | 4-C1 | CH | Et | Et | ||
| 2-166 | 4-Me | N | Me | SMe | 174-177 | |
| 2-167 | 4-C1 | N | SMe | SMe | 179-182 | |
| 2-168 | 4-Br | N | SMe | SMe | ||
| 2-169 | 4-Me | N | SMe | SMe | ||
| 2-170 | 4-C1 | N | OMe | SMe | ||
| 2-171 | 4-Me | N | OMe | SMe | ||
| 2-172 | 4-Me | N | OMe | Ph | 165-168 | |
| 2-173 | 4-C1 | N | NMe2 | NMe2 | >300 | |
| 2-174 | H | CBr | OMe | OMe | ||
| 2-175 | H | CMe | Cl | Cl | ||
| 2-176 | 4-Me | COMe | H | H | ||
| 2-177 | 4-C1 | COMe | H | H | ||
| 2-178 | 4-Me | N | Cl | Ph | 106-109 | |
| 2-179 | 4-C1 | N | Cl | Ph |
• · · » (Tabulka 58 )
| I sloučenina č. | Yn | A | R1 | R2 | m.p. (°C) nebo 0¾20) | |
| 2-180 | 4-Cl | CH | C=CMe | Me | ||
| 2-181 | 4-C1 | N | C^CMe | Me | ||
| 2-182 | 4-C1 | CH | ch=ch2 | Me | ||
| 2-183 | 4-C1 | N | ch=ch2 | Me | ||
| 2-184 | 4-C1 | CH | CHO | Me | ||
| 2-185 | 4-C1 | . N | CHO | Me | ||
| 2-186 | 4-C1 | CH | COMe | Me | ||
| 2-187 | 4-C1 | N | COMe | Me | ||
| 2-188 | 4-C1 | CH | CH2OMe | Me | ||
| 2-189 | 4-Me | CH | CH2OMe | Me | ||
| 2-190 | H | CH | CN | CN | ||
| 2-191 | H | CH | CN | Me | ||
| 2-192 | H | N | CN | CN | ||
| 2-193 | H | N | CN | Me | ||
| 2-194 | H | CH | SO2Me | SO2Me | ||
| 2-195 | H | N | SO2Me | SO2Me | ||
| 2-196 | H | CH | SO2Me | Me |
• · • · · · · · · · · • · · · « · * · ♦ • ······· · · · ♦ · • · · · · ♦ · · · (Tabulka 59 1
sloučenina
| č. | Yn | A |
| 3-1 | 3-Me | CH |
| 3-2 | 3-C1 | CH |
| 3-3 | 4-F | CH |
| 3-4 | 4-C1 | CH |
| 3-5 | 4-Br | CH |
| 3-6 | 4-Me | CH |
| 3-7 | 4-Bu-t | CH |
| 3-8 | 4-CF3 | CH |
| 3-9 | 4-OMe | CH |
| 3-10 | 4-OEt | CH |
| 3-11 | 4-OPr | CH |
| 3-12 | 4-0 CF3 | CH |
| 3-13 | 4-OCH2CH=CH2 | CH |
| 3-14 | 4-OCH2C=CH | CH |
| 3-15 | 4-OPh | CH |
| 3-16 | 4-OPh(4-Cl) | CH |
| 3-17 | 4-OPh(4-Me) | CH |
| 3-18 | 4-OPh(4-OMe) | CH |
| 3-19 | 4-SMe | CH |
| 3-20 | 4-CH20Me | CH |
| 3-21 | 4-COMe | CH |
| 3-22 | 4-COPh | CH |
| 3-23 | 4-CO2Et | CH |
| 3-24 | 4-Ph | CH |
| R1 | R2 | m.p. (°C) nebo RI ™ (1¾20) |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | 120-123 |
| OMe | OMe | |
| OMe | OMe | 117-118 |
| OMe | OMe | 128-129 |
| OMe | OMe | |
| OMe | OMe | 113-115 |
| OMe | OMe | |
| OMe | OMe | 129-132 |
| OMe | OMe | |
| OMe | OMe | 85-88 |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe | OMe | |
| OMe ' | OMe | |
| OMe | OMe | 130-132 |
(Tabulka 60 )
| 1 učeninž č. | Yn | A | R1 | R2 | m.p. (°C) nebo |
| 3-25 | 4-Ph(4-Cl) | CH | OMe | OMe | |
| 3-26 | 4-Ph(4-Me) | CH | OMe | OMe | |
| 3-27 | 4-Ph(4-OMe) | CH | OMe | OMe | |
| 3-28 | 4-NO2 | CH | OMe | OMe | |
| 3-29 | 4-NH2 | CH | OMe | OMe | |
| 3-30 | 4-NHMe | CH | OMe | OMe | |
| 3-31 | 4-NMe2 | CH | OMe | OMe | |
| 3-32 | 4-CN | CH | OMe | OMe | 166-169 |
| 3-33 | 5-F | CH | OMe | OMe | |
| 3-34 | 5-C1 | CH | OMe | OMe | 124-125 |
| 3-35 | 5-Me | CH | OMe | OMe | 91-94 |
| 3-36 | 5-CF3 | CH | OMe | OMe | |
| 3-37 | 5-OMe | CH | OMe | OMe | |
| 3-38 | 5-CO2Me | CH | OMe | OMe | |
| 3-39 | 5-COPh | CH | OMe | OMe | |
| 3-40 | 6-Me | CH | OMe | OMe | |
| 3-41 | 6-C1 | CH | OMe | OMe | |
| 3-42 | 4,5-Cl2 | CH | OMe | OMe | |
| 3-43 | 4,6-Me2 | CH | OMe | OMe | 145-147 |
| 3-44 | 4,5-Me2 | CH | OMe | OMe | |
| 3-45 | 4,5-(OMe)2 | CH | OMe | OMe | |
| 3-46 | 3-Br,5-CF3 | CH | OMe | OMe | |
| 3-47 | 3-Cl,5-CFs | CH | OMe | OMe | |
| 3-48 | 3,4,5-F3 | CH | OMe | OMe | |
| 3-49 | H | N | OMe | OMe | 152-155 |
| 3-50 | 3-Me | N | OMe | OMe | |
| 3-51 | 3-C1 | N | OMe | OMe | |
| 3-52 | 4-F | N | OMe | OMe | 183-186 |
| 3-53 | 4-C1 | N | OMe | OMe | 202-205 |
| 3-54 | 4-Br | N | OMe | OMe- | 200-203 |
| 3-55 | 4-1 | N | OMe | OMe | 191-194 . |
·· * • · · ♦ « ♦
(Tabulka 61 )
| 1 učenina č. | Yn. | A | R1 | R2 | m.p. (°C) nebo kb20) |
| 3-56 | 4-Me | N | OMe | OMe | 180-183 |
| 3-57 | 4-Et | N | OMe | OMe | 123-126 |
| 3-58 | 4-Pr | N | OMe | OMe | 136-139 |
| 3-59 | 4-CF3 | N | OMe | OMe | 177-180 |
| 3-60 | 4-Bu-t | N | OMe | OMe | 140-143 |
| 3-61 | 4-C=CBu-t | N | OMe | OMe | 161-164 |
| 3-62 | 4-OMe | N | OMe | OMe | 182-185 |
| 3-63 | 4-OEt | N | OMe | OMe | |
| 3-64 | 4-OPr | N | OMe | OMe | |
| 3-65 | 4-OCF3 | N | OMe | OMe | |
| 3-66 | 4-OCH2CH=CH2 | N | OMe | OMe | |
| 3-67 | 4-OCH2C=CH | N | OMe | OMe | |
| 3-68 | 4-OPh | N | OMe | OMe | |
| 3-69 | 4-SMe | N | OMe | OMe | |
| 3-70 | 4-COPh | N | OMe | OMe | 175-178 |
| 3-71 | 4-CO2Me | N | OMe | OMe | 197-200 |
| 3-72 | 4-Ph | N | OMe | OMe | |
| 3-73 | 4-Ph(4-Cl) | N | OMe | OMe | |
| 3-74 | 4-Ph(4-Me) | N | OMe | OMe . | |
| 3-75 | 4-Ph(4-OMe) | N | OMe | OMe | |
| 3-76 | 4-NO2 | N | OMe | OMe | |
| 3-77 | 4-NH2 | N | OMe | OMe | |
| 3-78 | 4-NHMe | N | OMe | OMe | |
| 3-79 | 4-NMe2 | N | OMe | OMe | 115-118 |
| 3-80 | 4-CN | N | OMe | OMe | 215-218 . |
| 3-81 | 5-F | N | OMe | OMe | |
| 3-82 | 5-C1 | N | OMe | OMe | |
| 3-83 | 5-Me | N | OMe | OMe | 131-134 |
| 3-84 | 5-CF3 | N | OMe | OMe | z |
| 3-85 | 5-OMe | N | OMe | OMe | |
| 3-86 | 5-NO2 | N | OMe | OMe |
(Tabulka62 )
| Γ~ sloučenina č. | Yn | A | R1 | R2 | m.p. (°C) nebo RI (¾20) | |
| 3-87 | 5-CO2Et | N | OMe | OMe | ||
| 3-88 | 5-COPh | N | OMe | OMe | ||
| 3-89 | 6-Me | N | OMe | OMe | ||
| 3-90 | 6-Cl | N | OMe | OMe | ||
| 3-91 | 4,5-(¾ | N | OMe | OMe | ||
| 3-92 | 4,5-Me2 | N | OMe | OMe | ||
| 3-93 | 4,5-(OMe)2 | N | OMe | OMe | ||
| 3-94 | 3-Br,5-CF3 | N | OMe | OMe | ||
| 3-95 | 3-Cl,5-CF3 | N | OMe | OMe | ||
| 3-96 | 3,4,5-F3 | N | OMe | OMe | ||
| 3-97 | 4-Me | N | OMe | OEt | 134-137 | |
| 3-98 | 4-C1 ' | N | OMe | OEt | 132-135 | |
| 3-99 | 4-Br | N | OMe | OEt | 140-142 | |
| 3-100 | H | CH | OEt | OEt | 146-148 | |
| 3-101 | 4-F | CH | OEt | OEt | ||
| 3-102 | 4-C1 | CH | OEt | OEt | ||
| 3-103 | 4-Br | CH | OEt | OEt | ||
| 3.-104 | 4-Me | CH | OEt | OEt | ||
| 3-105 | 4-CF3 | CH | OEt | OEt | 167-170 | |
| 3-106 | 4-F | N | OEt | OEt | ||
| 3-107 | 4-C1 | N | OEt | OEt | 163-166 | |
| 3-108 | 4-Br | N | OEt | OEt | 172-175 | |
| 3-109 | 4-Me | N | OEt | OEt | 158-161 | |
| 3-110 | 4-Bu-t | N | OEt | OEt | 128-129 | |
| 3-111 | 4-OMe | N | OEt | OEt | 128-129 | |
| 3-112 | 4-CF3 | N | OEt | OEt | ||
| 3-113 | 4-C1 | N | OPr | OPr | 145-148 | |
| 3-114 | 4-C1 | CH | OPr-i | OPr-i | ||
| 3-115 | 4-Me | CH | OPr-i | OPr-i | ||
| 3-116 | 4-C1 | N | OPr-i | OPr-i | 179-182 | |
| 3-117 | 4-Br | N | OPr-i | OPr-i |
0000
0
(Tabulka 63 )
| 1 oučenina č. | Yn | A | R1 | R2 | m.p. (°C) nébo |
| 3-118 | 4-C1 | N | 0CH2CH=CH2 | OCH2CH=CH2 | |
| 3-119 | 4-Br | N | och2ch=ch2 | och2ch=ch2 | |
| 3-120 | 4-Cl | N | och2c=ch | och2c=ch | |
| 3-121 | 4-Br | N | och2c=ch | och2c=ch | |
| 3-122 | 4-Cl | N | och2cn | och2cn | |
| 3-123 | 4-Br | N | och2cn | och2cn | |
| 3-124 | 4-Br | N | OCH2CH2OMe | OCH2CH2OMe | |
| 3-125 | 4-Cl | N | OCH2CH2OMe | OCH2CH2OMe | |
| 3-126 | 4-Br | N | OCH2Pr-c | OCH2Pr-c | |
| 3-127 | 4-C1 | N | OCH2Pr-c | OCH2Pr-c | 156-159 |
| 3-128 | H | CH | OBn | OBn | |
| 3-129 | H | N | OBn | OBn | |
| 3-130 | H | N | OBn(4-Cl) | OBn(4-Cl) | |
| 3-131 | H | N | OBn(4-Me) | OBn(4-Me) | |
| 3-132 | H | N | OBn(4-OMe) | OBn(4-OMe) | |
| 3-133 | H | CH | OMe | OPh | |
| 3-134 | H | N | OMe | OPh | |
| 3-135 | H | N | OMe | 0Ph(4-Cl) | |
| 3-136 | H | N | OMe | OPh(4-Me) | |
| 3-137 | H | N | OMe | OPh(4-OMe) | |
| 3-138 | H | CH | OMe | ochf2 | |
| 3-139 | H | N | OMe | ochf2 | |
| 3-140 | 4-C1 | CH | OMe | H | 136-139 |
| 3-141 | 4-Me | CH | OMe | H | 126-129 |
| 3-142 | 4-Cl | CH | OEt | H | 113-115 |
| 3-143 | 4-Me | CH | OEt | H | 103-105 |
| 3-144 | 4-Cl | CH | OMe | Me | |
| 3-145 | 4-Me | CH | OMe | Me | |
| 3-146 | 4-CFg | CH | OMe | Me | 134-137 |
| 3-147 | 4-Cl | N | OMe | Me | |
| 3-148 | 4-Me | N | OMe | Me | 202-205 |
··· ♦♦···· · · · • ♦ · · · ♦ · ♦ Μ «··· · * · · · · • ·····♦· ·♦ ♦ · · · • · * · · · · · · *0 · ·· 0 0· ♦··
Ί·ζ~ (Tabulka64 )
| 1 sloučenina ř | Yn | A | R1 | R2 | m.p. (°C) nebo RI | |
| (¾20) | ||||||
| 3-149 | 4-C1 | N | OMe | Pr | ||
| 3-150 | 4-Me | N | OMe | Pr | 133-136 | |
| 3-151 | 4-C1 | . N | OMe | Pr-c | ||
| 3-152 | 4-Br | N | OMe | Pr-c | 163-165 | |
| 3-153 | 4-Me | N | OMe | Pr-c | 56-59 | |
| 3-154 | 4-C1 | N | OEt | Pr-c | 163-166 | |
| 3-155 | 4-Me | N | OEt | Pr-c | 105-108 | |
| 3-156 | 4-C1 | N | OMe | Et | 155-158 | |
| 3-157 | 4-Br | N | OMe | Et | 162-165 | |
| 3-158 | 4-Me | N | OMe | Et | 171-174 | |
| 3-159 | 4-C1 | N | OEt | Et | ||
| 3-160 | 4-Br | N | OEt | Et | ||
| 3-161 | 4-Me | N | OEt | Et | ||
| 3-162 | 4-Me | N | OPr | Me | ||
| 3-163 | 4-C1 | N | OPr | Me | ||
| 3-164 | 4-Me | CH | Me | Et | 92-95 | |
| 3-165 | 4-C1 | CH | Me | Et | ||
| 3-166 | 4-Me | CH | Et | Et | 91-94 | |
| 3-167 | 4-C1 | CH | Et | Et | ||
| 3-168 | 4-Me | . N | Me | SMe | 180-183 | |
| 3-169 | 4-C1 | N | SMe | SMe | 192-195 | |
| 3-170 | 4-Br | N | SMe | SMe | ||
| 3-171 | 4-Me | N | SMe | SMe | ||
| 3-172 | 4-C1 | N | OMe | SMe | ||
| 3-173 | 4-Me | N | OMe | SMe | ||
| 3-174 | 4-Me | N | OMe | Ph | 170-173 | |
| 3-175 | 4-C1 | N | NMe2 | NMe2 | 176-179 | |
| 3-176 | H | CBr | OMe | OMe | ||
| 3-177 | H | CMe | Cl | Cl | ||
| 3-178 | 4-Me | COMe | H | H | ||
| 3-179 | 4-C1 | COMe | H | H |
• ♦ <···· • ·
(Tabulka 65 )
| 1 . ouěemna č. | Yn | A | R1 | R2 |
| 3-180 | 4-Me | N | Cl | Ph |
| 3-181 | 4-C1 | N | Cl | Ph |
| 3-182 | 4-C1 | CH | CsCMe | Me |
| 3-183 | 4-Cl | N | C^CMe | Me |
| 3-184 | 4-C1 | CH | CH=CH2 | Me |
| 3-185 | 4-Cl | N | ch=ch2 | Me |
| 3-186 | . 4-C1 | CH | CHO | Me |
| 3-187 | 4-C1 | N | CHO | Me |
| 3-188 | 4-C1 | CH | COMe | Me |
| 3-189 | 4-C1 | N | COMe | Me |
| 3-190 | 4-C1 | CH | CH2OMe | Me |
| 3-191 | 4-Me | CH | CHzOMe | Me |
| 3-192 | H | CH | CN | CN |
| 3-193 | H | CH | CN | Me |
| 3-194 | H | N | CN | CN |
| 3-195 | H | N | CN | Me |
| 3-196 | H | CH | SO2Me | SO2Me |
| 3-197 | H | N | SO2Me | SO2Me |
| 3-198 | H | CH | SO2Me | Me |
m.p. (°C) nebo
RI (no20)
PŘÍKLADY PROVEDENÍ VYNÁLEZU
Nyní budou specificky popsány postupy pro produkci sloučeniny předkládaného vynálezu, formulační metody a aplikace spolu s referencemi k příkladům.
PŘÍKLAD 1 l-(4-methoxypyrimidin-2-yl)-benzimidazol (sloučenina číslo 1-667)
Benzimidazol (0,50 g) se rozpustí v dimethylformamidu (10 ml) a do této směsi se přidá hydrid sodný (60% čistota, olejnatý) (0,18 g) za laboratorní teploty. Po třepání po dobu 1 hodiny se za laboratorní teploty přidá 2-chloro-4-methoxypyrimidin (0,62 g) a následuje třepání po dobu 3 hodin. Přidá se ledová voda a následuje extrakce ethyl acetátem, promytí saturovaným chloridem sodným ve vodném roztoku a usušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a zbytková látka je purifikována na koloně se silika gelem přičemž se získá 0,40 g požadovaného produktu jako bílého prášku (teplota tání 114-116 °C).
PŘÍKLAD 2
-(4,6-dimethoxyrpyrimidin-2-yl)-2-methylthiobenzimidazol (sloučenina číslo 1-4)
2-Methylthiobenzimidazol (0,50 g) se rozpustí v dimethylformamidu (10 ml) a do této směsi se za laboratorní teploty přidá hydrid sodný (60% čistota, olejnatý). Po třepání po dobu 1 hodiny se za laboratorní teploty přidá 2-methylsulfonyl-4,6-dimethoxypyrimidin (0,67 g) a následuje třepání po dobu 8 hodin. Přidá se ledová voda a následuje extrakce ethyl acetátem, promytí vodným roztokem saturovaného chloridu sodného a usušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum je purifíkováno na chromatografícké koloně se silika gelem, aby se získalo 0,80 g produktu jako bílého prášku (teplota tání 135-137 °C).
PŘÍKLAD 3 l-(4,6-dimethoxypyrimidin-2-yl)-2-methylsulfonylbenzimidazol (sloučenina číslo 1-5) l-(4,6-dimethoxypyrimidin-2-yl)-2-methylthiobenzimidazol (0,70 g) a kyselina mchloroperbenzová (1,30 g) se rozpustí v chloroformu (30 ml) a následuje třepání za laboratorní teploty po dobu 3 hodin. Reakční kapalina se promyje 5% vodným roztokem uhličitanu draselného a vrstva organického rozpouštědla se vysuší na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografícké koloně se silika gelem, aby se získalo 0,5 gramu požadovaného produktu jako bílého prášku (teplota tání 114117°C).
Ή
PŘÍKLAD 4 l-(4,6-dimethoxypyrimidin-2-yl)-2-methoxybenzimidazol (sloučenina číslo 1-18) l-(4,6-dimethoxypyrimidin-2-yl)-2-methoxybenzimidazol (0,40 g) se rozpustí v tetrahydrofuranu (20 ml) a za chlazení ledem se k této směsi přidá methylát sodný (0,50 g) a následuje třepání po dobu 1 hodiny. Přidá se ledová voda a následuje extrakce ethyl acetátem, promývání vodným roztokem saturovaného chloridu sodného a sušení na bezvodém síranu horečnatém. Rozpouštědlo se oddestiluje a směs se purifikuje na chromatografické koloně se silika gelem, aby se získalo 0,40 g požadovaného produktu jako bílý prášek (teplota tání 121-122 °C)
PŘÍKLAD 5 l-(4,6-dimethoxypyrimidin-2-yl)-2,5-dimethylbenzimidazol (sloučenina číslo 1-186)
N‘-4,6-dimethoxypyrimidin-2-yl)-4-methylbenzen-l,2-diamin (2,50 g) se rozpustí v kyselině octové (20 ml) a hydridu kyseliny octové (10 ml), následuje reflux po dobu 4 hodin. Přidá se voda a krystaly se seberou pomocí filtrace, promyjí se vodou a usuší. Provede se rekrystalizace z ethanolu, aby se získalo 1,90 g požadovaného produktu jako bílé pří podobné krystalky (teplota tání 163-166 °C).
PŘÍKLAD 6
2-amino-l-(4,6-dimethoxypyrimidin-2-yl)-5-methylbenzimidazol (sloučenina číslo 1-362)
N‘-(4,6-dimethoxypyrimidin-2-yl)-4-methylbenzen-l,2-diamin (2,00 g) se rozpustí v ethanolu a za laboratorní teploty se přidá bromid kyanogenu (1,00 g), následuje třepání při 60 °C po dobu 1 hodiny. Přidá se voda a krystaly se seberou filtrací, promyjí se vodou a vysuší se, aby se získalo 2,3 g produktu jako bílý prášek (teplota tání alespoň 300 °C).
PŘÍKLAD 7
2-chloro-l-(4,6-dimethoxypyrimidin-2-yI)-5-methylbenzimidazol (sloučenina číslo 1-258)
2-Amino-l-(4,6-dimethoxypyrimidin-2-yl)-5-methylbenzimidazol (1,67 g) a chlorid měďnatý (0,94 g) se vloží do acetonitrilu (30 ml) a za laboratorní teploty se přidá tert-butyl nitrit (0,9 g), následuje reflux po dobu 30 minut. Přidá se voda, následuje extrakce ethyl acetátem, promytí vodným roztokem saturovaného chloridu sodného a vysušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografické koloně se silika gelem, aby se získalo 1,48 g požadovaného produktu jako bílých peří podobných krystalků (teplota tání 145-148 °C).
• · • · · • ·
Ή
·· «·«· • « ♦
PŘÍKLAD 8
-(4,6-dimethoxypyrimidin-2-yl)-5-methyl-2-trifluoromethylbenzimidazol (sloučenina číslo I298)
Anilid 2-(4,6-dimethoxypyrimidin-2-yl)amino-5-methyltrifluor octové kyseliny (0,6 g) a kyselina paratoluensulfonová (0,05 g) se rozpustí v toluenu (30 ml), následuje reflux po dobu 5 hodin. Přidá se voda a ethyl acetát a organická vrstva se promyje roztokem saturovaného hydrogenuhličtanu sodného a vodným roztokem saturovaného chloridu sodného a vysuší se na bezvodém sulfátu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografické koloně se silika gelem, aby se získalo 0,56 požadovaného výsledného produktu jako bílý prášek (teplota tání 93-96 °C).
PŘÍKLAD 9 l-(4,6-dichloro-[l,3,5]triazin-2-yl)-2-methylbenzimidazol (sloučenina číslo 1-1066)
2-Methylbenzimidazol (5,0 g)se rozpustí v tetrahydrofuranu (50 ml) a k tomu se za laboratorní teploty přidá hydrid sodný (60% čistota, olejnatý) (1,60 g) po třepání po dobu 1 hodiny se za laboratorní teploty přidá kyanur chlorid (7,0 g), následuje třepání po dobu 3 hodin. Přidá se ledová voda, následuje extrakce ethyl acetátem, promytí vodným roztokem saturovaného chloridu sodného a vysušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografické koloně se silika gelem, aby se získalo 2,6 g požadovaného produktu jako bílý prášek (teplota tání alespoň 300 °C).
PŘÍKLAD 10 l-(4,6-dimethylthio-[l,3,5]triazin-2-yl)-2-methylbenzimidazol (sloučenina Číslo 1-1042) l-(4,6-dichloro-[l,3,5]triazin-2)-2-methylbenzimidazol (0,5 g) se rozpustí v methanolu (10 ml) a za laboratorní teploty se přidá 15% vodný roztok sodné soli methyl mercaptanu, následuje třepání podobu 1 hodiny. Po dokončení reakce se reakční kapalina nalije do studené vody a takto vzniklé krystaly se seberou filtrací, promyjí se vodou a vysuší se za vzniku 0,46 g požadovaného produktu jako bílý prášek (teplota tání 176-179 °C).
PŘÍKLAD 11
5-chloro-l-(4,6-dimethoxy-[l,3,5]triazin-2-yl)-2-methylbenzimidazol (sloučenina číslo 1-215)
4-chloro-N-(4,6-dimethoxy-[l,3,5]triazin-z-2-yl)benzen-l,2-diamin (0,5 g) se rozpustí v kyselině octové (10 ml) a anhydridu kyseliny octové (10 ml) a následuje reflux po dobu 4
Λχλ φφ· *φ χθ Φ Φ Φ Φ ΦΦ
Ο » » φφΦΦ φ Φi φφφ ·· φφ ·Φ· ·*·· ΦΦΦ • Φ 9ΦΦ · ΦΦ φ Φ Φ ·· φ ΦΦΦ « ΦΦ ΦΦΦ hodin. Přidá se voda a krystaly se seberou filtrací, promyjí se vodou a usuší. Rekrystalizace z ethanolu se provede za vzniku 0,47 g požadovaného produktu jako bílé peří podobné krystaly (teplota tání 173-176 °C).
PŘÍKLAD 12
5-chloro-l-(4,6-dimethoxy[l,3,5]triazin-2-yl)-2-methylbenzimidazol (sloučenina číslo 1-215) 2-Nitro-4-chloro-N-(4,6-dimethoxy-[l,3,5]triazin-2-yl) anilin (0,5 g) a železitý prášek (0,3 g) se rozpustí v kyselině octové (10 ml) a anhydridu kyseliny octové (5 ml), následuje reflux po dobu 4 hodin. Reakční směs se ochladí na laboratorní tepotu a následuje filtrace. Filtrát se koncentruje za sníženého tlaku, k reziduu se přidá voda a krystaly se seberou filtrací, promyjí se vodou a usuší. Rekrystalizace z ethanolu se provede za vzniku 0,39 g požadovaného produktu jako bílé peří podobné krystaly (teplota tání 173-176 °C).
PŘÍKLAD 13
2-amino-5-chloro-l-(4,6-dimethoxy-[l,3,5]triazin-2-yl)benzimidazol (sloučenina číslo 1-368)
4-chloro-N -(4,6-dimethoxy-[l,3,5]triazin-2-yl)benzen-l,2-diamin (1,5 g) se rozpustí v ethanolu (50 ml) a za laboratorní teploty se k tomu přidá kyanogen bromidu (0,6 g), následuje třepání při 60°C po dobu 1 hodiny. Přidá se voda, krystaly se seberou filtrací, promyjí se vodou a vysuší za vzniku 1,2 g požadovaného produktu jako růžový prášek (teplota tání 293-296 °C).
PŘÍKLAD 14
2,5-dichloro-l-(4,6-dimethoxy-[l,3,5]triazin-2-yl)benzimidazol (sloučenina číslo 1-277) 2-Amino-5-chloro-l-(4,6-dimethoxy-[l,3,5]triazin-2-yl)benzimidazol (1,1 g) a chlorid měďnatý (0,6 g) se vloží do acetonitrilu (50 ml) a za laboratorní teploty se k tomu přidá tertbutyl nitrit (0,5 g), následuje reflux po dobu 30 minut. Přidá se voda, následuje extrakce ethyl acetátem, promytí vodným roztokem saturovaného chloridu sodného a vysušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografické koloně se silika gelem za vzniku 0,5 g požadovaného produktu jako bílé peří podobné krystaly (teplota tání 146-149 °C).
PŘÍKLAD 15 l-(4,6-dimethoxy-[l,3,5]triazin-yl)-5-methyl-2-trifluoromethylbenzimidazol (sloučenina číslo I312)
| • 1 | 9 | ···· | 99 | |||
| • · | • | * · · | 9 | 9 | 99 | |
| • | • | • · | • 9 9 | 9 9 | 9 | |
| • | • | ···· | • · 9 9 | 9 9 | 9 | 9 |
| • | • | • | • · · | • | • | 9 |
| 9Λ | • | ·· 9 | • 9 | 999 |
Anilid 2-(4,6-dimethoxy-[l,3,5]triazin-2-yl)amino-5-methyltrifluoroctové kyseliny (1,0
g) a kyselina paratoluensulfonová (0,05 g) se rozpustí v chlorbenzenu (30 ml), následuje reflux po dobu 5 hodin. Přidá se voda a ethyl acetát a organická vrstva se promyje roztokem saturovaného hydrogenuhličitanu sodného a vodným roztokem saturovaného chloridu sodného a vysuší se na bezvodém síranu hořečnatém. Rozpouštědlo se oddestíluje a reziduum se purifikuje na chromatografické koloně se silika gelem za vzniku 0,23 g požadovaného produktu jako bílý prášek (teplota tání 137-140 °C).
Nyní budou níže uvedena data 'H-NMRfCDCh/TMS, δ (ppm) týkající se některých příkladů sloučenin podle předkládaného vynálezu.
$Λ_
| ( Tabulka 6 6) | |
| l-------------------------------------- Sloučenina č. | 1H-NMR Ó (ppm) , rozpouštědlo CDC13 |
| 1-30 | 2.99(6H,s);4.03(6H,s);5.99(lH,s);7.03-7.09(lH,m);7.17-7.22(lH,m); 7.48-7.51(lH,m),‘7.84-7.85(lH,m);8.01(lH,s) |
| 1-34 | 3.64(6H,s);5.92(lH,s);7.42-7.36(5H,m);7.56-7.60(2H,ni); 7.58-7.88(lH,m);8.20-8.23(lH,m) |
| 1-840 | 1.41(6H,d,J=6.3Hz);2.52(3H,s);2.98(3H,s);5.39-5.47(lH,m); 6.46(lH,s);7.26-7.33(2H,m);7.69-7.72(lH,m);8.25-8.28(lH,m) |
| 1-872 | 1.01(3H,t,J=7.5Hz);;1.49-1.57(2H,m);1.80-1.87(2H,m);2.51(3H,s); 4.50(2H,t,J=6.57Hz);6.45(lH,s);7.33-7.43(2H,m);7.82-7.85(lH,m); 8.55-8.59(lH,m);9.05(lH,s) |
| 1-906 | i:66-2.11(8H,m);2.45(3H,s);5.51-5.56(lH,m);6.36(lH,s); 7.28-7.41(2H,m);7.81-7.83(lH,m);;8.45-8.52(lH,m);9.05(lH,s) |
| 1-907 | 1.65-2.04(8H,m);2.51(3H,s);3.98(3H,s);5.51-5.55(lH,m);6.46(lH,s); 7.26-7.34(2H,m);7.68-7.73(lH,m);8.25-8.31(lH,m) |
| 1-959 | 1.03(3H,t,J=7.41Hz);1.81-1.89(2H,m);2.76(2H,t,J=7.14Hz); 3.00(3H,s);4.08(3H,s);6.51(lH,s);7.27-7.33(2H,m);7.70-7.73(lH,m); 8.28-8.34(lH,m) |
| 1-960 | 1.03(3H,t,J=7.29Hz);1.81-1.89(2H,m);2.77(2H,t,J=7.29Hz); 4.07(3H,s);6.58(lH,s);7.30-7.37(2H,m);7.71-7.74(lH,m); 8.00-8.05(lH,m) |
• · ř z ········ · · j i i <a 3 ·..· : ·..· : ..
Nyní bude níže uvedena příprava příkladů meziproduktů pro syntézu sloučenin předkládaného vynálezu.
PŘÍKLAD 16
N-(4,6-dimethoxypyrimidin-2-yl)-4-methyl-2-nitroanilin (sloučenina číslo 2-6)
N-formyl-4-methyl-2-nitroanilin (25,00 g) se rozpustí v dimethylformamidu (400 ml) a ktomu se za laboratorní teploty přidá hydrid sodný (60% čistota, olejnatý) (6,11 g). Po třepání po dobu 10 minut se za laboratorní teploty přidá 2-methylsulfonyl-4,6-dimethoxypyrimidin (30,28 g), následuje třepání po dobu 3 hodin. Ktomu se přidá 10% vodný roztok NaOH a krystaly se seberou filtrací, promyjí se vodou a vysuší za vzniku 37,5 g požadovaného produktu jako žlutý prášek (teplota tání 158-161 °C).
PŘÍKLAD 17
N‘-(4,6-dimethoxypyrimidin-2-yl)-4-methylbenzen-l,2-diamin (sloučenina číslo 3-6)
N-(4,6-dimethoxypyrimidin-2-yl)-4-methyl-2-nitroanilin (37,5 g) se rozpustí v ethyl acetátu (600 ml) a ktomu se přidá 10% paladnatý uhlík (3,75 g). Třepání se provádělo za laboratorní teploty při normálním tlaku ve vodíkové atmosféře po dobu 4 hodin, následovala filtrace. Rozpouštědlo filtrátu bylo oddestilováno, aby se získalo 32,70 g požadovaného produktu jako bílý prášek (teplota tání 128-129 °C).
PŘÍKLAD 18
Anilid 2-(4,6-dimethoxypyrimidin-2-yl)amino-5-methyltrifluor octové kyseliny (sloučenina číslo 1-196)
N,-(4,6-dimethoxypyrimidin-2-yl)-4-methylbenzen-l,2-diamin (0,80 g) se rozpustí v pyridinu (10 ml) a za chlazení ledovou solí se přidává anhydrid kyseliny trifluoroctové (0,97 g). Po třepání po dobu 1 hodiny se přidá neředěná kyselina chlorovodíková, následuje extrakce ethyl acetátem, promytí ředěnou kyselinou chlorovodíkovou a vodným roztokem saturovaného chloridu sodného a sušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifíkuje na chromatografické koloně se silika gelem, aby se získalo 0,88 g požadovaného produktu jako bílý prášek (teplota tání 144-147 °C).
PŘÍKLAD 19
N-(4,6-dimethoxy-[l,3,5]triazin-2-yl)-4-methyl-2-nitroanilin (sloučenina číslo 2-56) • · · · ni ···· · · · · ’T
Jz/z. · ······· ·· · ♦ ··
·..· : ·..· :.· ·ί
N-formyl-4-methyl-2-nitroanilin (7,2 g) se rozpustí v tetrahydrofuranu (50 ml) a do toho se za laboratorní teploty přidá hydrid sodný (60% čistota, olejnatý) (2,0 g). Po třepání po dobu 10 minut se za laboratorní teploty přidá 2-chloro-4,6-dimethoxy-(l,3,5)triazin (7,0 g), následuje třepaní po dobu 3 hodin. K tomu se přidá 10% vodný roztok hydroxidu sodného a krystaly se seberou filtrací, promyjí se vodou, vysuší, aby se získalo 10,0 g požadovaného produktu jako žlutý prášek (teplota tání 189-191 °C).
PŘÍKLAD 20
N‘-(4,6-dimethoxy-(l,3,5)triazin-2-yl)-4-methylbenzen-l,2-diamin (sloučenina číslo 3-56) N-(4,6-dimethoxy-[l,3,5]triazin-2-yl)-4-methyl-2-nitroanilin (10 g) se rozpustí v ethyl acetátu (50 ml) a vodě (50 ml) a k tomu se přidá 10 g železitého prášku a kyselina octová (2 ml), následuje reflux po dobu 2 hodin. Nerozpustný materiál se odstraní filtrací a vrstva ethyl acetátu se promyje saturovaným vodným roztokem chloridu sodného a vysuší se na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje, aby se získalo 8,8 g požadovaného produktu jako bílý prášek (teplota tání 180-183 °C).
PŘÍKLAD 21
Anilid 2-(4,6-dimethoxy-[l,3,5]triazin-2-yl)amino-5-methyltrifluoroctové kyseliny (sloučenina číslo 1-210)
N‘-(4,6-dimethoxy-[l,3,5]triazin-2-yl)-4-methylbenzen-l,2-diamin (1,0 g) se rozpustí v pyridinu (50 ml) a zachlazením ledovou solí se k tomu přidá anhydrid kyseliny trifluoroctové (0,8 g). Po třepání po dobu 1 hodiny se ktomu přidá naředěná kyselina chlorovodíková, následuje extrakce ethyl acetáte, promytí naředěnou kyselinou chlorovodíkovou a saturovaným vodným roztokem chloridu sodného a sušení na bezvodém síranu hořečnatém. Rozpouštědlo se oddestiluje a reziduum se purifikuje na chromatografické koloně se silika gelem, aby se získalo 1,3 g požadovaného produktu jako bílý prášek (teplota tání 195-198 °C).
PŘÍKLAD 22
4-chloro-N-(4,6-dimethoxy-[l,3,5]triazin-2-yl)-2-nitroanilin (sloučenina číslo 2-53) 4-chloro-2-nitroanilin (5,0 g) a hydrogenuhličitan sodný (3,6 g) se rozpustí v tetrahydrofuranu (50 ml) a k tomu se přidá kyanur chlorid (8,0 g), následuje třepání po dobu 8 hodin. Do reakčního roztoku se přidá 28% mehylát sodný (11,2 g) a následuje reflux po dobu 1 hodiny. Ktomu se přidá voda, následuje extrakce ethyl acetátem, promytí saturovaným vodným roztokem chloridu sodného a sušení na bezvodém síranu hořečnatém. Rozpouštědlo se • ·
Λ—- ···· · · ··· ýk · ····· 9 9 9 9 9 99
ΟΟ ··· 9 · ··
9 99 ·999 oddestiluje a reziduum se vystaví rekrystalizaci z ethanolu, aby se získalo 6,3 g požadovaného produktu jako žlutý prášek (teplota tání 206-208 °C).
Zemědělské a zahradnické fungicidy podle předkládaného vynálezu obsahují deriváty triazinylbenzimidazolu reprezentované obecným vzorcem I jako aktivní látky. Jsou-li sloučeniny předkládaného vynálezu použity pro zemědělské/zahradnické fungicidy, aktivní látka může být použita ve vhodné formulaci v závislosti na účelu a aktivní látka je většinou naředěna v inertním kapalném nebo pevném nosiči a je použita ve vhodné dávkovači formě jako je prach, smáčivý prášek, emulzifikovatelný koncentrát nebo granulát, které se smísí se surfaktantem nebo jinými látkami v závislosti na jejich použití.
Výhodné příklady nosičů zahrnují pevné nosiče jako je mastek, bentonit, hlína, kaolín, rozsivková zemina, bílé uhlí, vermikulit, hašené vápno, síran amonný, křemičitý písek a močovina, a kapalné nosiče jako je izopropylalkohol, xylen, cyklohexan a metylnaftalen. Příklady surfaktantů a disperzních látek zahrnují dinaftylmethansulfonáty, estery solí kyseliny alkohol-sírové, alkylarylsulfonáty, lignin sulfonáty, ether polyoxyethylen glykolu, alkyl aryl ethery polyoxyethylenu a polyoxyethylen sorbitan monoalkylát. Příklady adjuvants zahrnují karboxymethylcelulózu a podobné látky. Tyto formulace jsou aplikovány po naředění na vhodnou koncentraci nebo přímo.
Zemědělské/zahradnické fungicidy podle předkládaného vynálezu mohou být použity pro listovou léčbu, půdní léčbu nebo hloubkovou léčbu. Směsný poměr aktivní látky je vhodně vybrán v závislosti na tom kterém případu. Avšak výhodná proporce se pohybuje od 0,1 do 20% (váhových) v případech prachu nebo granulí, a od 5 do 80% (váhových) v případech emulzifíkačních koncentrátů nebo smáčivých prášků. Dávka zemědělských/zahradnických fungicidů podle předkládaného vynálezu závisí na typu použité sloučeniny, na chorobě, která má být kontrolována, na tendenci choroby rozvíjet se, na stupni poškození, enviromentálních podmínkách a typu formulace, která je použita. Například pro přímé použití jako prach nebo granule se dávka aktivní látky vybírá tak, aby se vhodně pohybovala v rozmezí od 0,1 g do 5 kg, výhodně od 1 g do 1 kg na 10 arů. Pro použití v kapalném stavu jako emulzifikující koncentrát nebo smáčivý prášek se dávka vybírá vhodně v rozmezí od 0,1 ppm do 10 000 ppm, výhodně od 1 do 3000 ppm.
Sloučeniny podle předkládaného vynálezu ve výše uvedených formulacích mohou kontrolovat rostlinné choroby vyvolané Oomycéty, Ascomycéty, Deuteromycéty a
Basidiomycéty. Specifické příklady mikroorganismů jsou uvedeny níže, ale vynález není omezen jen na ně. Rod Pseudoperonospora jako je Pseudoperonospora cubensis, rod Erysipfe jako je Erysipfe graminis, rod Venturia jako je Venturia inaegualis,rod Pyricularia jako je • ·
Λ/ · · · · ·· ♦ ··
JtL-k · · ···· · · · · · · · ··· · · · · · ·· · ·· · ·· ·
Pyricularia oryzae, rod Botrytis jako je Botrytis cinerea, rod Rhizoctonia jako je Rhizoctonia solani a rod Pucciniajako je Puccinia recondita.
Sloučeniny podle předkládaného vynálezu mohou být použity v kombinaci s insekticidy, jinými fungicidy, herbicidy, regulátory rostlinného růstu nebo fertilizéry, jak ten který případ vyžaduje. Nyní budou s odkazem na příklady popsány typické formulace zemědělských/zahradnických fungicidů dle předkládaného vynálezu. Odtud dále v dokumentu „%“ znamená „váhové %“.
FORMULACE PŘÍKLADU 1 prach % sloučeniny (1-45), 5 % rozsivkové zeminy a 93 % hlíny se rovnoměrně smísily a rozmělnily, aby byl získán prach.
FORMULACE PŘÍKLADU 2 smáčivý prášek % sloučeniny (1-170), 45 % rozsivkové zeminy, 2 % dinaphthylmethandisulfonátu sodného a 3 % lignin sulfonátu sodného se rovnoměrně smísily a rozmělnily za vzniku smáčí vého prášku.
FORMULACE PŘÍKLADU 3 emulzifikující koncentrát % sloučeniny (1-309), 20 % cyklohexanonu, 11 % alky aryl etheru polyoxyethylenu, 4 % alkylbenzensulfonátu vápenatého a 35 % methylnapthalenu se rovnoměrně rozpustilo za vzniku emulzifíkujícího koncentrátu.
FORMULACE PŘÍKLADU 4 granule % sloučeniny (1-121), 2 % sodné soli sírového esteru lauryl alkoholu, 5 % lignin sulfonátu sodného, 2 % karboxymethylcelulózy a 86 % hlíny se rovnoměrně smísilo a rozmělnilo. Vzniklá směs se hnětla s 20 % vody, byla granulována na velikost ok v síti 4 až 32 ve smyslu extruzního granulátoru a byla vysušena za vzniku granulí.
Nyní budou se vztahem ke specifickému testovanému příkladu popsány účinky zemědělských/zahradnických fungicidů dle předkládaného vynálezu.
TESTOVACÍ PŘIKLAD 1 Test pro preventivní účinek a prachovou plíseň pšenice semen pšenice (varieta: Norin-61-go) bylo vyseto v každém květináči z polyvinylchloridu o rozměrech 9 cm x 9 cm a nechaly se růst ve skleníku po dobu 8 dní, pak byly léčeny 10 ml na květináč vodným roztokem smáčivého prášku připraveného v souladu
9
s Formulací příkladu 2, v koncentraci 500 ppm ve smyslu aktivní látky a sušeny na vzduchu. Poté byly sazenice inokulovány sporami Erysiphe graminis pokropením rostliny a ta byla umístěna do skleníku o teplotě od 20 do 25 °C. 10 dní po inokulaci s celková plocha choroby na prvních listech v každém květináči sledovala a hodnotila na základě standardů uvedených v tabulce 67. Výsledky jsou uvedeny v tabulkách 68 a 69.
Tabulka 67
| Hodnocení | |
| A | bez oblasti s chorobou |
| B | oblast s chorobou méně než 25% |
| C | oblast s chorobou alespoň 25%, ale méně než 50% |
| D | oblast s chorobou alespoň 50% |
Zemědělské/zahradnické fungicidy podle předkládaného vynálezu mají široké spektrum kontroly chorob a mají vynikající účinek obzvláště u práškové plísně pšenice. Dále mají vysoký kontrolní účinek na měkkou plíseň okurek, svrabovitost jablek, šedou plíseň okurek, nákazu pochev rýže a hnědou listovou rez pšenice, a jsou vynikající v reziduální účinnosti a odolnosti k dešti bez toho, že by ničily plodiny, proto jsou užitečnými zemědělskými/zahradnickými fungicidy.
| • · • | • • | ♦< ···· • · · | ·· • · · |
| • | • · | • · ♦ | • · |
| • | • · · · | • · · · | • · · |
| • | • · · | • · | |
| • · | • | ·· · | ·· · |
(Tabulka 68 )
| sloučenina | biologická | sloučenina | biologická | sloučenina |
| č. | účinnost | č. | účinnost | č. |
| 1-1 | A | 1-189 | A | 1-307 |
| 1-2 | A | 1-192 | B | 1-309 |
| 1-3 | A | 1-195 | B | 1-310 |
| 1-6 | B | 1-199 | B | 1-311 |
| 1-7 | A | 1-200 | A | 1-312 |
| 1-10 | B | 1-201 | A | 1-313 |
| 1-22 | A | 1-202 | B | 1-314 |
| 1-23 | A | 1-203 | B | 1-315 |
| 1-25 | A | 1-204 | A | 1-316 |
| 1-26 | A | 1-208 | B | 1-318 |
| 1-27 | B | 1-209 | B | 1-321 |
| 1-29 | B | 1-212 | B | 1-327 |
| I-3O | B | 1-214 | A | 1-332 |
| 1-35 | B | 1-215 | A | 1-333 |
| 1-38 | B | 1-216 | A | 1-334 |
| 1-40 | B | 1-217 | , A | 1-335 |
| 1-41 | A | 1-218 | A | 1-336 |
| 1-45 | A | 1-219 | A | 1-346 |
| 1-66 | A | 1-220 | B | 1-358 |
| 1-82 | A | 1-221 | B | 1-359 |
| 1-83 | B | 1-222 | B | 1-360 |
| 1-84 | A | 1-225 | A | 1-362 |
| 1-85 | A | 1-226 | A | 1-364 |
| 1-87 | A | 1-229 | A | 1-366 |
| 1-88 | B | 1-232 | B | 1-368 |
| 1-91 | B | 1-234 | A | 1-369 |
| 1-111 | B | 1-235 | A | 1-375 |
| 1-112 | B | 1-239 | A | 1-376 |
| 1-113 | B | 1-242 | A | 1-377 |
| 1-114 | B | 1-250 | B | 1-378 |
| 1-116 | B | 1-251 | A | 1-379 |
| 1-122 | B | 1-255 | A | 1-380 |
| 1-130 | A | 1-256 | A | 1-381 |
| 1-131 | A | 1-258 | A | 1-388 |
| 1-132 | A | 1-259 | A | 1-389 |
| 1-133 | A | 1-260 | A | 1-394 |
| 1-134 | A | 1-261 | B | 1-400 |
| 1-135 | A | 1-263 | A | 1-404 |
| 1-136 | B | 1-271 | A | 1-405 |
| 1-141 | A | 1-272 | A | 1-406 |
| 1-175 | A | 1-277 | B | 1-423 |
| 1-176 | A | 1-279 | A | 1-424 |
| 1-181 | B | 1-295 | A | 1-438 |
| 1-183 | B | 1-296 | A | 1-457 |
| 1-184 | A | 1-298 | A | 1-458 |
| 1-185 | A | 1-299 | A | 1-461 |
| 1-186 | A | 1-300 | A | 1-462 |
| 1-188 | A | 1-301 | A | 1-465 |
biologická účinnost
(Tabulka 69 )
| sloučenina č. | biologická účinnost | sloučenina č. | biologická účinnost | sloučenina v c. |
| 1-479 | A | 1-752 | A | 1-1088 |
| 1-480 | A | 1-758 | A | 1-1090 |
| 1-482 | A | 1-762 | A | 1-1093 |
| 1-483 | A | 1-767 | B | 1-1094 |
| 1-486 | A | 1-768 | A | 1-1095 |
| 1-490 | A | 1-769 | A | 1-1096 |
| 1-498 | A | 1-771 | A | 1-1098 |
| 1-499 | A | 1-772 | A | 1-1103 |
| 1-501 | A | 1-775 | A | 1-1104 |
| 1-502 | A | 1-804 | A | 11106 |
| 1-503 | A | 1-805 | B | 1-1123 |
| 1-507 | A | 1-806 | B | 1-1147 |
| 1-508 | B | 1-809 | B | |
| 1-510 | A | 1-818 | B | |
| 1-511 | A | 1-831 | B | |
| 1-514 | A | 1-839 | A | |
| 1-515 | A | 1-840 | B | |
| 1-516 | A | 1-872 | B | |
| 1-530 | A | 1-883 | A | |
| 1-531 | A | 1-885 | B | |
| 1-534 | A | 1-894 | B | |
| 1-543 | A | 1-895 | B | |
| 1-544 | A | 1-903 | B | |
| 1-545 | A | 1-904 | B | |
| 1-546 | A | 1-915 | A | |
| 1-550 | A | 1-958 | B | |
| 1-573 | B | 1-959 | A | |
| 1-580 | A | 1-960 | A | |
| 1-592 | A | 1-962 | A | |
| 1-595 | B | 1-964 | B | |
| 1-601 | A | 1-965 | A | |
| 1-667 | B | 1-967 | A | |
| 1-669 | B | 1-999 | A | |
| 1-670 | B | 1-1004 | A | |
| 1-671 | B | 1-1019 | A | |
| 1-672 | B | 1-1022 | A | |
| 1-675 | B | 1-1043 | A | |
| 1-682 | A | 1-1046 | A | |
| 1-683 | A | 1-1048 | A | |
| 1-690 | A | 1-1058 | A | |
| 1-692 | B | 1-1059 | A | |
| 1-693 | A | 1-1064 | B | |
| 1-694 | B | 1-1071 | A | |
| 1-695 | A | 1-1079 | B | |
| 1-704 | B | 1-1082 | B | |
| 1-705 | A | 1-1085 | A | |
| 1-726 | B | 1-1086 | B | |
| 1-731 | B | 1-1087 | A |
biologická účinnost
Claims (8)
- ·· ····PATENTOVÉ NÁROKY1. Derivát pyrimidinylbenzimidazolu nebo triazinylbenzimidazolu, reprezentovaný obecným vzorcem I {kde A je N nebo CR3, každý z R1 a R2, které jsou nezávisle na sobě atom vodíku, halogen, (Ci- -C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-Có) alkinylová skupina, (C3-C6) cykloalkylová skupina, (C1-C4) haloalkylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-Ce) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (Cj-C4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3- -Cď) cykloalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (CiC6) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (C1-C4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-Q,) alkylsulfonyl skupina, R3 je atom vodíku, (Ci- -Cg) alkylová skupina, (Ci-Ce) alkoxyskupina nebo halogen, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Ci-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C]-C6) alkylthioskupina, (C]-C6) alkylsulfonyl skupina, fenoxyskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, anilinová • · φφ ·-71 φ φ · φ · φ · φ φφ φ φφφ φφφ skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (CiC4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (C]-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-Ce) alkinylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (CiC4) haloalkylová skupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(CrC4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}.
- 2. Derivát pyrimidinylbenzimidazolu podle nároku 1, kde A ve výše uvedeném obecném vzorci je CR3.
- 3. Derivát triazinylbenzimidazolu podle nároku 1, kde A ve výše uvedeném obecném vzorci je N.
- 4. Derivát pyrimidinylbenzimidazolu reprezentovaný obecným vzorcem I, kde A je CR3, každý z R1 a R2, které jsou nezávisle na sobě atom vodíku, halogen, (C]-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, (C1-C4) haloalkylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (C1-C4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3-C6) cyklóalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (Ci- -C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (Ci-C6) alkylthioskupina, (CiC4) alkoxy (C1-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (CiC4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-Cg) alkylsulfonyl skupina, R3 je atom vodíku, (Ci-Cg) alkylová skupina, (Cj-Cg) alkoxyskupina nebo halogen, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Cj-Cg) alkylová skupina, (C2-Cg) alkenylová skupina, (C2Cg) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (CrCe) alkylthioskupina, (C]-Cg) alkylsulfonyl skupina, fenoxyskupina, (C1-C4) alkoxy (Ci• · ·· · • · · · · · ♦ ··QO · ···*··· ·· · ··V Z, ·«· · · · ·♦ ·» · ·· * *·C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (CrC4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, aminoskupina, mono(CiC4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, anilinová skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (C]-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C]--C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (Cr C4) haloalkylová skupina, (CrC4) alkylkarbonylová skupina, (CrC4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (Ci-C4) alkylovou skupinou nebo (CrC4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C]-C4) alkylovou skupinou nebo (CrC4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}.
- 5. Derivát triazinylbenzimidazolu reprezentovaný obecným vzorcem I, kde A je N, každý z R a R , které jsou nezávisle na sobě atom vodíku, halogen, (Ci-Ce) alkylová skupina, (C2-Ce) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, (Ci-C4) haloalkylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (CrC4) haloalkoxyskupina, kyano (Ci-C4) alkoxyskupina, (Ci-C4) alkoxy (Ci-C4) alkyloxyskupina, (C3-C6) cykloalkyl (Ci-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (Ci- -C4) alkylovou skupinou nebo (C]-C4) alkoxyskupinou], (C]-C6) alkylthioskupina, (CiC4) alkoxy (C]-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (Ci-C4) alkylovou skupinou nebo (Ci-C4) alkoxyskupinou], (CiC4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-C6) alkylsulfonyl skupina, R3 je atom vodíku, (Ci-C6) alkylová skupina, (CrC6) alkoxyskupina nebo halogen, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Ci-CíJ alkylová skupina, (C2-Cď) alkenylová skupina, (C2Cg) alkinylová skupina, (C3-Cé) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (Ci-C4) alkylovou skupinou nebo (Ci-C4) alkoxyskupinou], alkoxyskupina, (C2-Ce) alkenyloxyskupina, (C2-Cf,) alkinyloxyskupina, (C]-C6) alkylthioskupina, (Ci-C6) alkylsulfonyl skupina, fenoxyskupina, (Ci-C4) alkoxy (CiC4) alkylová skupina, (Ci-C4) haloalkylová skupina, (Ci-C4) haloalkoxyskupina, (Ci-C4) alkylkarbonylová skupina, (Ci-C4) alkoxykarbonylová skupina, aminoskupina, mono(Ci * · * 4 * *C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, anilinová skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (C(-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (CrC4) alkylthioskupina, (Cj-C4) alkoxy (C1-C4) alkylová skupina, (CjC4) haloalkylová skupina, (C1-C4) alkylkarbonylová skupina, (Cj-C4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}.
- 6. Derivát anilinpyrimidinu reprezentovaný obecným vzorcem XV (XV)1 7 · [kde každý z R a R , které jsou nezávisle na sobě atom vodíku, halogen, (Ci-Cé) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, (C1-C4) haloalkylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2- -C6) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (C1-C4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3-C6) cykloalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (Cj- -C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (Ci-C6) alkylthioskupina, (Cj-C4) alkoxy (C1-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (C1-C4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, • e »·i« _ . ««*·······94 · ····*·* ·· * · · * · · · · · · a·· • •v a· a ·♦· »·· di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-C6) alkylsulfonyl skupina, R3 je atom vodíku, (C]-C6) alkylová skupina, (C]-C6) alkoxyskupina nebo halogen, R5 je aminoskupina, nitro skupina nebo -NHCOX, X je atom vodíku, halogen, nitro skupina, kyano skupina, (Ci-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (Ci-C6) alkylthioskupina, (C]-C6) alkylsulfonyl skupina, fenoxyskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, aminoskupina, mono(C]C4) alkylaminoskupina, di(C]-C4) alkylaminoskupina, anilínová skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (Ci-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-Cé) alkinylová skupina, (Ci-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-Ce) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C!-C4) alkoxy (C1-C4) alkylová skupina, (CiC4) haloalkylová skupina, (Cj- -C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C1--C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}, přičemž R5 je nitro skupina, každý z R1 a R2 jsou nezávisle na sobě fluor, brom, jod, (Ci-Cf,) alkylová skupina, (C2-C6) alkenylová skupina, (C2-Cé) alkinylová skupina, (C3-C6) cykloalkylová skupina, (C1-C4) haloalkylová skupina, (Cj-Cg) alkoxyskupina, (C2-Ce) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (C]-C4) alkoxyskupina, (C1-C4) alkoxy (C]-C4) alkyloxyskupina, (C3- -C6) cykloalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (CiCď) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (C]-C4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-C6) alkylsulfonyl skupina}.·· ····
- 7. Derivát anílinpyrimidinu reprezentovaný obecným vzorcem XVII každý zR1 a R2, které jsou nezávisle na sobě atom vodíku, halogen, (Ci-Ce) alkylová skupina, (C2-C6) alkenylová skupina, (C2-Cé) alkinylová skupina, (C3-C6) cykloalkylová skupina, (Cj-C4) haloalkylová skupina, (C]-C6) alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C3-C6) cykloalkoxyskupina, (C1-C4) haloalkoxyskupina, kyano (C1-C4) alkoxyskupina, (C1-C4) alkoxy (C1-C4) alkyloxyskupina, (C3-C6) cykloalkyl (C1-C4) alkyloxyskupina, benzyloxyskupina [uvedená skupina může být substituována halogenem, (Ci- -C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (Ci-C6) alkylthioskupina, (CiC4) alkoxy (C]-C4) alkylová skupina, fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], (CjC4) alkylkarbonylová skupina, formylová skupina, fenylová skupina, di(Ci-C4) alkylaminoskupina, kyano skupina nebo (Ci-C6) alkylsulfonyl skupina, R3 je atom vodíku, (Ci-C6) alkylová skupina, (CrC6) alkoxyskupina nebo halogen, X je atom vodíku, halogen, nitro skupina, kyano skupina, (C]-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2C6) alkinylová skupina, (C3-C6) cykloalkylová skupina, benzylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (Ci-Cé) alkylthioskupina, (Cj-Cf,) alkylsulfonyl skupina, fenoxyskupina, (C1-C4) alkoxy (CiC4) alkylová skupina, (C1-C4) haloalkylová skupina, (C1-C4) haloalkoxyskupina, (Ci-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina, aminoskupina, mono(CiC4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, anilinová skupina nebo fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou], Y je halogen, nitro skupina, kyano skupina, (Cj-C6) alkylová skupina, (C2-C6) alkenylová skupina, (C2-C6) alkinylová skupina, (C]-C6) ··· ······ ·· ··· ·· · · · · ···· ·· · ·· • ······· · · ·· · alkoxyskupina, (C2-C6) alkenyloxyskupina, (C2-C6) alkinyloxyskupina, (C1-C4) haloalkoxyskupina, (C1-C4) alkylthioskupina, (C1-C4) alkoxy (C1-C4) alkylová skupina, (CiC4) haloalkylová skupina, (C1-C4) alkylkarbonylová skupina, (C1-C4) alkoxykarbonylová skupina., benzoyl skupina, aminoskupina, mono(Ci-C4) alkylaminoskupina, di(Ci-C4) alkylaminoskupina, fenylová skupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (C1-C4) alkoxyskupinou] nebo fenoxyskupina [uvedená skupina může být substituována halogenem, (C1-C4) alkylovou skupinou nebo (Cj-C4) alkoxyskupinou], a n je 0 nebo celé číslo od 1 do 3}.
- 8. Zemědělský/zahradnický fungicid obsahující derivát pyrimidinylbenzimidazolu nebo triazinylbenzimidazolu, jak je definováno v nárocích 1,2,3,4 nebo 5, jako aktivní složku.
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| EP0264348B1 (de) | 1986-10-13 | 1993-12-15 | Ciba-Geigy Ag | Harnstoffe |
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| RU2037491C1 (ru) * | 1992-12-30 | 1995-06-19 | Пятигорский фармацевтический институт | Производные 4-оксо-1,4-дигидропиримидина, обладающие иммуностимулирующей активностью |
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-
1999
- 1999-11-15 CZ CZ20011466A patent/CZ20011466A3/cs unknown
- 1999-11-15 PL PL99347688A patent/PL194045B1/pl not_active IP Right Cessation
- 1999-11-15 SK SK615-2001A patent/SK286264B6/sk not_active IP Right Cessation
- 1999-11-15 NZ NZ511311A patent/NZ511311A/xx not_active IP Right Cessation
- 1999-11-15 CA CA002350968A patent/CA2350968C/en not_active Expired - Fee Related
- 1999-11-15 HU HU0104171A patent/HUP0104171A3/hu unknown
- 1999-11-15 DE DE69927516T patent/DE69927516T2/de not_active Expired - Lifetime
- 1999-11-15 IL IL14315799A patent/IL143157A0/xx unknown
- 1999-11-15 KR KR1020017005888A patent/KR100631307B1/ko not_active Expired - Fee Related
- 1999-11-15 RU RU2001116600/04A patent/RU2222536C2/ru not_active IP Right Cessation
- 1999-11-15 TR TR2001/01381T patent/TR200101381T2/xx unknown
- 1999-11-15 BR BRPI9915401-3A patent/BR9915401B1/pt not_active IP Right Cessation
- 1999-11-15 AU AU11805/00A patent/AU755538B2/en not_active Ceased
- 1999-11-15 AT AT99972212T patent/ATE305465T1/de not_active IP Right Cessation
- 1999-11-15 WO PCT/JP1999/006364 patent/WO2000029404A1/ja active IP Right Grant
- 1999-11-15 US US09/830,578 patent/US6576631B1/en not_active Expired - Fee Related
- 1999-11-15 EP EP99972212A patent/EP1132387B1/en not_active Expired - Lifetime
- 1999-11-15 CN CNB998154881A patent/CN1243002C/zh not_active Expired - Fee Related
-
2001
- 2001-05-15 IL IL143157A patent/IL143157A/en not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE305465T1 (de) | 2005-10-15 |
| IL143157A0 (en) | 2002-04-21 |
| US6872729B2 (en) | 2005-03-29 |
| HUP0104171A3 (en) | 2002-04-29 |
| PL194045B1 (pl) | 2007-04-30 |
| HUP0104171A2 (hu) | 2002-02-28 |
| US20040023966A1 (en) | 2004-02-05 |
| KR20010080976A (ko) | 2001-08-25 |
| RU2222536C2 (ru) | 2004-01-27 |
| AU1180500A (en) | 2000-06-05 |
| KR100631307B1 (ko) | 2006-10-04 |
| DE69927516D1 (de) | 2006-02-09 |
| CN1243002C (zh) | 2006-02-22 |
| TR200101381T2 (tr) | 2002-05-21 |
| AU755538B2 (en) | 2002-12-12 |
| EP1132387A4 (en) | 2002-06-05 |
| SK286264B6 (sk) | 2008-06-06 |
| CA2350968C (en) | 2008-10-28 |
| SK6152001A3 (en) | 2001-12-03 |
| US6576631B1 (en) | 2003-06-10 |
| EP1132387A1 (en) | 2001-09-12 |
| EP1132387B1 (en) | 2005-09-28 |
| WO2000029404A1 (fr) | 2000-05-25 |
| NZ511311A (en) | 2002-10-25 |
| BR9915401A (pt) | 2001-08-14 |
| CA2350968A1 (en) | 2000-05-25 |
| PL347688A1 (en) | 2002-04-22 |
| BR9915401B1 (pt) | 2011-04-19 |
| IL143157A (en) | 2010-11-30 |
| CN1333768A (zh) | 2002-01-30 |
| WO2000029404A8 (fr) | 2000-09-08 |
| DE69927516T2 (de) | 2006-03-16 |
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