TWI326283B - Method for preparing fused oxazinones - Google Patents
Method for preparing fused oxazinones Download PDFInfo
- Publication number
- TWI326283B TWI326283B TW092118080A TW92118080A TWI326283B TW I326283 B TWI326283 B TW I326283B TW 092118080 A TW092118080 A TW 092118080A TW 92118080 A TW92118080 A TW 92118080A TW I326283 B TWI326283 B TW I326283B
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- och2cf3
- group
- ochf2
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 83
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical class O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- -1 pyridine compound Chemical class 0.000 claims abstract description 96
- 239000000203 mixture Substances 0.000 claims abstract description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 39
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract 9
- 239000000460 chlorine Substances 0.000 claims description 823
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 150000001804 chlorine Chemical class 0.000 claims 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 108
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 60
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 56
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 47
- 239000002585 base Substances 0.000 description 46
- 239000002904 solvent Substances 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 229910052799 carbon Inorganic materials 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 125000000623 heterocyclic group Chemical group 0.000 description 26
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 25
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 125000003118 aryl group Chemical group 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 125000004122 cyclic group Chemical group 0.000 description 22
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 238000007792 addition Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 125000002837 carbocyclic group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- 239000001301 oxygen Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 229910052717 sulfur Chemical group 0.000 description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 102220088038 rs727502896 Human genes 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 229910052721 tungsten Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000006612 decyloxy group Chemical group 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000007667 floating Methods 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000003880 polar aprotic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40035202P | 2002-07-31 | 2002-07-31 | |
| US44643803P | 2003-02-11 | 2003-02-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200410962A TW200410962A (en) | 2004-07-01 |
| TWI326283B true TWI326283B (en) | 2010-06-21 |
Family
ID=31191366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092118080A TWI326283B (en) | 2002-07-31 | 2003-07-02 | Method for preparing fused oxazinones |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7339057B2 (enExample) |
| EP (1) | EP1549643B1 (enExample) |
| JP (1) | JP2006501203A (enExample) |
| KR (1) | KR101050872B1 (enExample) |
| CN (1) | CN100422177C (enExample) |
| AT (1) | ATE371657T1 (enExample) |
| AU (1) | AU2003257028B2 (enExample) |
| BR (1) | BR0313341A (enExample) |
| DE (1) | DE60316006T2 (enExample) |
| ES (1) | ES2293040T3 (enExample) |
| IL (1) | IL165503A (enExample) |
| TW (1) | TWI326283B (enExample) |
| WO (1) | WO2004011447A2 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| MY142967A (en) * | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| DE60226875D1 (de) | 2001-08-15 | 2008-07-10 | Du Pont | Orthosubstituierte arylamide zur bekämpfung von wirbellosen schädlingen |
| US7199138B2 (en) | 2001-08-16 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| TWI343376B (en) * | 2002-07-31 | 2011-06-11 | Du Pont | Method for preparing 3-halo-4, 5-dihydro-1h-pyrazoles |
| AU2003295491B2 (en) * | 2002-11-15 | 2009-10-08 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
| WO2004067528A1 (en) | 2003-01-28 | 2004-08-12 | E.I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
| KR20060008336A (ko) * | 2003-06-12 | 2006-01-26 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 융합된 옥사지논 제조 방법 |
| US7317124B2 (en) | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
| US20050124666A1 (en) * | 2003-11-13 | 2005-06-09 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same |
| US7126026B2 (en) | 2003-11-13 | 2006-10-24 | Sanofi-Aventis Deutschland Gmbh | Process for preparing 4-pentafluorosulfanylbenzoylguanidines |
| WO2005118552A2 (en) * | 2004-04-13 | 2005-12-15 | E.I. Dupont De Nemours And Company | Anthranilamide insecticides |
| JP5215669B2 (ja) | 2004-11-18 | 2013-06-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | アントラニルアミド殺虫剤 |
| TWI363756B (en) | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| KR20080005438A (ko) * | 2005-04-20 | 2008-01-11 | 신젠타 파티서페이션즈 아게 | 시아노 안트라닐아미드 살충제 |
| UA89546C2 (uk) | 2005-07-07 | 2010-02-10 | Басф Се | N-tioантраніламідні сполуки, способи їх одержання, застосування для боротьби та спосіб боротьби з паразитами, спосіб захисту рослин, спосіб лікування тварин, композиція та спосіб її одержання |
| MX2008002236A (es) * | 2005-08-24 | 2008-03-27 | Du Pont | Antranilamidas para controlar plagas de invertebrados. |
| MX2009002960A (es) | 2006-09-21 | 2009-06-26 | Activx Biosciences Inc | Inhibidores de serina hidrolasa. |
| CN102134238A (zh) * | 2010-01-25 | 2011-07-27 | 中化蓝天集团有限公司 | 一种含一氟甲氧基吡唑的4h-苯并[1,3]噁嗪-4-酮类化合物、其制备方法及应用 |
| CN102285971B (zh) * | 2010-06-21 | 2013-12-18 | 中国中化股份有限公司 | 吡唑基喹唑啉酮类化合物及其应用 |
| CN102260245A (zh) * | 2011-06-02 | 2011-11-30 | 南开大学 | 2,3-二氢喹唑啉酮类衍生物及其制备方法和应用 |
| US20140171316A1 (en) | 2011-08-12 | 2014-06-19 | Basf Se | Anthranilamide compounds and their use as pesticides |
| CN103842342A (zh) | 2011-08-12 | 2014-06-04 | 巴斯夫欧洲公司 | 邻氨基苯甲酰胺化合物及其作为农药的用途 |
| BR112014003221A2 (pt) | 2011-08-12 | 2017-04-18 | Basf Se | composto da fórmula geral (i), método para preparação de um comporto da fórmula (i), composição agrícola ou veterinária, métodos para combater ou controlar pragas invertebradas, para a proteção de plantas em crecimento contra o ataque ou infestação por pragas invertebradas, para a proteção de sementes contra insetos terrestres e das raízes e galhos de mudas contra insetos terrestres e foliares, semente, uso de um composto e método para tratamento de um animal infestado ou infectado por parasitas ou para evitar que animais fiquem infestados ou infectados por parasitas ou para proteção de um animal contra infestação ou infecção por parasitas |
| BR112014003111A2 (pt) * | 2011-08-12 | 2017-02-21 | Basf Se | processo para preparar um composto de 1h-pirazol-5- carbonilcloreto n-substituído e processo para preparar um composto de sulfimina |
| BR112014003112A2 (pt) | 2011-08-12 | 2017-02-21 | Basf Se | composto da fórmula geral (i), métodos para preparar um composto da fórmula (i), composição agrícola ou veterinária, método para combater ou controlar pragas invertebradas, método para proteger o cultivo de plantas, método para a proteção de sementes, semente, usos de um composto e método para tratar um animal |
| BR112014003595A2 (pt) | 2011-08-18 | 2017-03-01 | Basf Se | compostos, método de preparação de um composto, composição agrícola, método de combate ou controle de pestes invertebradas, métodos de proteção do crescimento de plantas e de proteção de sementes, semente, uso de um composto e método de tratamento de animal infestado |
| BR112014003646A2 (pt) | 2011-08-18 | 2017-03-07 | Basf Se | composto de fórmula (i), método para preparar um composto de fórmula (i), composição agrícola ou veterinária, método para combater ou controlar pragas invertebradas do grupo de insetos, aracnídeos ou nematoides, método para proteger plantas, método para a proteção de semente, semente e método para tratar um animal infestado ou infectado por parasitas |
| EP2744785A1 (en) | 2011-08-18 | 2014-06-25 | Basf Se | Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests |
| CN104487439B (zh) | 2012-05-24 | 2017-06-09 | 巴斯夫欧洲公司 | N‑硫代邻氨基苯甲酰胺化合物及其作为杀害虫剂的用途 |
| US8987461B2 (en) | 2012-12-06 | 2015-03-24 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| CN106366046B (zh) * | 2016-08-29 | 2019-12-31 | 鲁南制药集团股份有限公司 | 一种新利司他的制备方法 |
| CN106366047B (zh) * | 2016-08-31 | 2019-12-31 | 鲁南制药集团股份有限公司 | 一种一锅法制备新利司他的方法 |
| CN107033135B (zh) * | 2017-05-26 | 2020-09-11 | 浙江省诸暨合力化学对外贸易有限公司 | 一种制备异噁嗪酮化合物的方法及其应用 |
| CN108033944B (zh) * | 2017-12-28 | 2020-10-16 | 利尔化学股份有限公司 | 氯虫苯甲酰胺杂质制备工艺 |
| CN108689988A (zh) * | 2018-06-22 | 2018-10-23 | 南开大学 | 含n-芳基吡咯的邻甲酰氨基苯甲酰胺类化合物与制备方法和应用 |
| CN113692406B (zh) | 2019-02-18 | 2024-07-23 | Pi工业有限公司 | 制备邻甲酰胺基苯甲酰胺类化合物及其中间体的方法 |
| CN111825653A (zh) | 2019-04-19 | 2020-10-27 | 安道麦马克西姆有限公司 | 取代吡唑类化合物的制备及其作为邻氨基苯甲酰胺前体的用途 |
| CN111423431B (zh) * | 2020-04-01 | 2022-10-28 | 利尔化学股份有限公司 | 一种氯虫苯甲酰胺及其中间体的制备方法 |
| UY39391A (es) | 2020-08-24 | 2022-03-31 | Adama Makhteshim Ltd | Proceso para la preparación de pirazoles sustituidos |
| TW202222162A (zh) | 2020-09-26 | 2022-06-16 | 印度商皮埃企業有限公司 | 鄰胺苯甲酸／醯胺化合物及其中間體的合成方法 |
| CA3223599A1 (en) | 2021-08-19 | 2023-02-23 | Peter FINKBEINER | Method for controlling diamide resistant pests & compounds therefor |
| WO2023110710A1 (en) * | 2021-12-13 | 2023-06-22 | Syngenta Crop Protection Ag | Method for controlling diamide resistant pests & compounds therefor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07309851A (ja) * | 1994-05-16 | 1995-11-28 | Fuji Chem Ind Co Ltd | ベンゾオキサジノン誘導体の製造方法 |
| US5932726A (en) * | 1996-12-16 | 1999-08-03 | Dupont Pharmaceuticals Company | Asymmetric synthesis of benzoxazinones |
| CA2285000A1 (en) * | 1997-04-07 | 1998-10-15 | Dupont Pharmaceuticals Company | Asymmetric synthesis of benzoxazinones via new intermediates |
| MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| AU2002227243A1 (en) * | 2000-12-11 | 2002-06-24 | E.I. Du Pont De Nemours And Company | Quinazolinones and pyridinopyrimidinones for controlling invertebrate pests |
| AR036872A1 (es) * | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| TWI371450B (en) * | 2001-08-13 | 2012-09-01 | Du Pont | Novel substituted dihydro 3-halo-1h-pyrazole-5-carboxylates,their preparation and use |
| MY142967A (en) * | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| AU2002319814A1 (en) | 2001-08-13 | 2003-03-03 | E.I. Du Pont De Nemours And Company | Substituted 1h-dihydropyrazoles, their preparation and use |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| TWI343376B (en) | 2002-07-31 | 2011-06-11 | Du Pont | Method for preparing 3-halo-4, 5-dihydro-1h-pyrazoles |
-
2003
- 2003-07-02 TW TW092118080A patent/TWI326283B/zh not_active IP Right Cessation
- 2003-07-29 ES ES03772097T patent/ES2293040T3/es not_active Expired - Lifetime
- 2003-07-29 DE DE60316006T patent/DE60316006T2/de not_active Expired - Lifetime
- 2003-07-29 AU AU2003257028A patent/AU2003257028B2/en not_active Ceased
- 2003-07-29 WO PCT/US2003/023821 patent/WO2004011447A2/en not_active Ceased
- 2003-07-29 EP EP03772097A patent/EP1549643B1/en not_active Expired - Lifetime
- 2003-07-29 BR BR0313341-9A patent/BR0313341A/pt not_active IP Right Cessation
- 2003-07-29 US US10/518,324 patent/US7339057B2/en not_active Expired - Lifetime
- 2003-07-29 KR KR1020057001577A patent/KR101050872B1/ko not_active Expired - Fee Related
- 2003-07-29 CN CNB038182025A patent/CN100422177C/zh not_active Expired - Lifetime
- 2003-07-29 AT AT03772097T patent/ATE371657T1/de not_active IP Right Cessation
- 2003-07-29 JP JP2004524204A patent/JP2006501203A/ja active Pending
-
2004
- 2004-12-01 IL IL165503A patent/IL165503A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60316006T2 (de) | 2008-05-15 |
| US20050215785A1 (en) | 2005-09-29 |
| KR20050026534A (ko) | 2005-03-15 |
| CN100422177C (zh) | 2008-10-01 |
| ES2293040T3 (es) | 2008-03-16 |
| BR0313341A (pt) | 2005-07-12 |
| WO2004011447A3 (en) | 2004-03-18 |
| US7339057B2 (en) | 2008-03-04 |
| KR101050872B1 (ko) | 2011-07-20 |
| AU2003257028B2 (en) | 2010-12-09 |
| EP1549643B1 (en) | 2007-08-29 |
| JP2006501203A (ja) | 2006-01-12 |
| AU2003257028A1 (en) | 2004-02-16 |
| EP1549643A2 (en) | 2005-07-06 |
| IL165503A (en) | 2010-11-30 |
| TW200410962A (en) | 2004-07-01 |
| CN1671703A (zh) | 2005-09-21 |
| ATE371657T1 (de) | 2007-09-15 |
| IL165503A0 (en) | 2006-01-15 |
| DE60316006D1 (de) | 2007-10-11 |
| WO2004011447A2 (en) | 2004-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |