EA020918B1 - 4-фенилпиран-3,5-дионы, 4-фенилтиопиран-3,5-дионы и 2-фенилциклогексан-1,3,5-трионы в качестве гербицидов - Google Patents

Info

Publication number

EA020918B1

EA020918B1 EA201000888A EA201000888A EA020918B1 EA 020918 B1 EA020918 B1 EA 020918B1 EA 201000888 A EA201000888 A EA 201000888A EA 201000888 A EA201000888 A EA 201000888A EA 020918 B1 EA020918 B1 EA 020918B1

Authority

EA

Eurasian Patent Office

Prior art keywords

formula

compound

alkyl

mixture

hydrogen

Prior art date

2007-12-13

Links

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• Global Dossier
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• 239000004009 herbicide Substances 0.000 title claims abstract description 14
• MWZWKEXOAFTLCK-UHFFFAOYSA-N 2-phenylcyclohexane-1,3,5-trione Chemical class O=C1CC(=O)CC(=O)C1C1=CC=CC=C1 MWZWKEXOAFTLCK-UHFFFAOYSA-N 0.000 title 1
• HAJHBDMUSIUKKR-UHFFFAOYSA-N 4-phenyloxane-3,5-dione Chemical class O=C1COCC(=O)C1C1=CC=CC=C1 HAJHBDMUSIUKKR-UHFFFAOYSA-N 0.000 title 1
• MILPANKGEKZHKH-UHFFFAOYSA-N 4-phenylthiane-3,5-dione Chemical class O=C1CSCC(=O)C1C1=CC=CC=C1 MILPANKGEKZHKH-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 936
• -1 g is 0) Chemical compound 0.000 claims description 674
• 239000000203 mixture Substances 0.000 claims description 274
• 229910052739 hydrogen Inorganic materials 0.000 claims description 121
• 239000001257 hydrogen Substances 0.000 claims description 120
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
• 239000002904 solvent Substances 0.000 claims description 57
• 229910052760 oxygen Inorganic materials 0.000 claims description 51
• 150000002431 hydrogen Chemical class 0.000 claims description 47
• 238000000034 method Methods 0.000 claims description 42
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 238000002360 preparation method Methods 0.000 claims description 38
• 239000002585 base Substances 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 241000196324 Embryophyta Species 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 25
• 229910052700 potassium Inorganic materials 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 18
• 229910052763 palladium Inorganic materials 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 239000003054 catalyst Substances 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 239000003446 ligand Substances 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 240000008042 Zea mays Species 0.000 claims description 8
• 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 239000011630 iodine Substances 0.000 claims description 8
• 230000000873 masking effect Effects 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229920000742 Cotton Polymers 0.000 claims description 7
• 239000000729 antidote Substances 0.000 claims description 7
• 230000002363 herbicidal effect Effects 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 235000005822 corn Nutrition 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• 235000013339 cereals Nutrition 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 3
• 239000007848 Bronsted acid Substances 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 235000010469 Glycine max Nutrition 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 230000012010 growth Effects 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
• 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 2
• 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
• 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 2
• 244000068988 Glycine max Species 0.000 claims description 2
• 240000000111 Saccharum officinarum Species 0.000 claims description 2
• 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
• 235000021536 Sugar beet Nutrition 0.000 claims description 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 244000045561 useful plants Species 0.000 claims description 2
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 240000000385 Brassica napus var. napus Species 0.000 claims 1
• 241000219146 Gossypium Species 0.000 claims 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
• 230000009286 beneficial effect Effects 0.000 claims 1
• CZVTYGFISHLVHK-UHFFFAOYSA-N 4h-pyran-2,3-dione Chemical compound O=C1CC=COC1=O CZVTYGFISHLVHK-UHFFFAOYSA-N 0.000 abstract description 2
• SJSBKIXOCNOEFF-UHFFFAOYSA-N 2h-thiopyran 1,1-dioxide Chemical compound O=S1(=O)CC=CC=C1 SJSBKIXOCNOEFF-UHFFFAOYSA-N 0.000 abstract 1
• SUEVWEWAIVZWCQ-UHFFFAOYSA-N cyclohexane-1,2,3-trione Chemical class O=C1CCCC(=O)C1=O SUEVWEWAIVZWCQ-UHFFFAOYSA-N 0.000 abstract 1
• FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 699
• 239000011541 reaction mixture Substances 0.000 description 164
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 154
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 126
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 118
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 106
• 239000000243 solution Substances 0.000 description 97
• 239000000706 filtrate Substances 0.000 description 82
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 69
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
• 239000007787 solid Substances 0.000 description 60
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
• 239000012074 organic phase Substances 0.000 description 53
• 238000010898 silica gel chromatography Methods 0.000 description 51
• 239000007864 aqueous solution Substances 0.000 description 46
• 238000006243 chemical reaction Methods 0.000 description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
• 239000003921 oil Substances 0.000 description 40
• 235000019198 oils Nutrition 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 229910052757 nitrogen Inorganic materials 0.000 description 31
• 239000005909 Kieselgur Substances 0.000 description 30
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000004480 active ingredient Substances 0.000 description 29
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• 239000000284 extract Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 239000008346 aqueous phase Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 239000010410 layer Substances 0.000 description 19
• 239000004094 surface-active agent Substances 0.000 description 19
• 239000012299 nitrogen atmosphere Substances 0.000 description 18
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 239000000725 suspension Substances 0.000 description 16
• 239000000654 additive Substances 0.000 description 15
• JGBZTJWQMWZVNX-UHFFFAOYSA-N palladium;tricyclohexylphosphane Chemical compound [Pd].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 JGBZTJWQMWZVNX-UHFFFAOYSA-N 0.000 description 15
• 239000012071 phase Substances 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
• BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 12
• MBWKWLJANJFDHT-UHFFFAOYSA-N 4-oxabicyclo[3.2.1]oct-6-ene Chemical compound C1COC2C=CC1C2 MBWKWLJANJFDHT-UHFFFAOYSA-N 0.000 description 10
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• 238000013459 approach Methods 0.000 description 10
• 239000012230 colorless oil Substances 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 9
• 238000004090 dissolution Methods 0.000 description 9
• 239000012153 distilled water Substances 0.000 description 9
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 8
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
• 239000000546 pharmaceutical excipient Substances 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 7
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 7
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 7
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 7
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 7
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 7
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 7
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 7
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 7
• SQLKXUKAJYHRNP-UHFFFAOYSA-N 4-bromo-2-ethylbenzaldehyde Chemical compound CCC1=CC(Br)=CC=C1C=O SQLKXUKAJYHRNP-UHFFFAOYSA-N 0.000 description 7
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 7
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 7
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 7
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 7
• 150000001502 aryl halides Chemical class 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 7
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 7
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 7
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 7
• XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 6
• 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
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• 244000299507 Gossypium hirsutum Species 0.000 description 6
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