JP5637650B2 - 複素環化合物 - Google Patents
複素環化合物 Download PDFInfo
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- JP5637650B2 JP5637650B2 JP2007118644A JP2007118644A JP5637650B2 JP 5637650 B2 JP5637650 B2 JP 5637650B2 JP 2007118644 A JP2007118644 A JP 2007118644A JP 2007118644 A JP2007118644 A JP 2007118644A JP 5637650 B2 JP5637650 B2 JP 5637650B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 18
- -1 amine compound Chemical class 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HCWHRICVTBCTKK-UHFFFAOYSA-N 2-bromo-4-hexyl-5-iodo-1,3-thiazole Chemical compound CCCCCCC=1N=C(Br)SC=1I HCWHRICVTBCTKK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PIVGHHIOIHDPRB-UHFFFAOYSA-N 2-bromo-4-hexyl-1,3-thiazole Chemical compound CCCCCCC1=CSC(Br)=N1 PIVGHHIOIHDPRB-UHFFFAOYSA-N 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- UVZFMRJLKLQNDI-UHFFFAOYSA-N 2-chloro-4-hexyl-1,3-thiazole Chemical compound CCCCCCC1=CSC(Cl)=N1 UVZFMRJLKLQNDI-UHFFFAOYSA-N 0.000 description 2
- NVXXGZWHLSDSMF-UHFFFAOYSA-N 2-chloro-4-hexyl-5-iodo-1,3-thiazole Chemical compound CCCCCCC=1N=C(Cl)SC=1I NVXXGZWHLSDSMF-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- WEIHTWYIJMCQOT-UHFFFAOYSA-N 4-hexyl-1,3-thiazol-2-amine Chemical compound CCCCCCC1=CSC(N)=N1 WEIHTWYIJMCQOT-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000005294 bicycloheptyloxy group Chemical group C1(CCCCCC1)(C1CCCCCC1)O* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 2
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 2
- 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 2
- 125000006612 decyloxy group Chemical group 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000005921 isopentoxy group Chemical group 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005484 neopentoxy group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 2
- 125000006611 nonyloxy group Chemical group 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- 125000005295 norbornyloxy group Chemical group C12(CCC(CC1)C2)O* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005447 octyloxy 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])O* 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005499 phosphonyl group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000005976 1-phenylethyloxy group Chemical group 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- MJIKNOFUEADIAA-UHFFFAOYSA-N CCCCCC(CC1(C)C)c2c1[s]c(C(C)(C)CC)n2 Chemical compound CCCCCC(CC1(C)C)c2c1[s]c(C(C)(C)CC)n2 MJIKNOFUEADIAA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 125000005070 decynyl 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#C* 0.000 description 1
- VHZAFVKQNYAKRA-UHFFFAOYSA-L dichloronickel;phenyl(3-phenylphosphanylpropyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1PCCCPC1=CC=CC=C1 VHZAFVKQNYAKRA-UHFFFAOYSA-L 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000005468 isobutylenyl group Chemical group 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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Description
〔式中、X及びYは相異なり、塩素原子、臭素原子、ヨウ素原子、CF3SO3−、CH3SO3−、C6H5SO3−又はCH3C6H4SO3−である。R1は置換されていてもよい炭素数2以上の1価の脂肪族炭化水素基である。A1及びA2は、一方が−S−、−O−、−Se−又は−Te−であり、他方が−N=、−P=又は−Si(R2)=(ここで、R2は、水素原子、置換されていてもよい1価の炭化水素基、ハロゲン原子、アミノ基又はカルボニル基である。)である。2本存在する実線と破線の平行線は、一方が単結合であり、他方が二重結合である。〕
で表される複素環化合物を提供する。
本発明の複素環化合物は、前記一般式(I)で表されるものである。
本発明の複素環化合物は、如何なる方法で合成されたものであってもよいが、その純度と合成効率の観点から、下記一般式(II):
〔式中、R1、A1、A2、及び2本存在する実線と破線の平行線は前記と同じ意味である。〕
で表される複素環化合物から、以下の第一の工程及び/又は第二の工程を含む方法、好ましくは第一の工程及び第二の工程を含む方法で合成することが好ましい。以下、2段階の反応を詳細に説明する。
〔式中、X、Y、R1、及び2本存在する実線と破線の平行線は前記と同じ意味を表す。〕
で表されるチアゾール化合物の合成を一例として、前述の第一の工程、第二の工程を具体的に説明する。
〔式中、R1、及び2本存在する実線と破線の平行線は前記と同じ意味を表す。〕
で表されるアミン化合物を、例えば、(1)亜硝酸アルキルとの撹拌及び(2)ハロゲン化水素又はハロゲン化金属との撹拌を連続又は同時に行うことにより、アミノ基を脱離しハロゲン原子を付加して、下記一般式(IIIa):
〔式中、X、R1、及び2本存在する実線と破線の平行線は前記と同じ意味を表す。〕
で表される化合物を合成することができる。亜硝酸アルキルの使用量は、前記アミン化合物1モルに対して、通常、1〜2モルであり、好ましくは1〜1.3モルである。ハロゲン化水素又はハロゲン化金属の使用量は、前記アミン化合物1モルに対して、通常、1〜5モルであり、好ましくは1〜3モルである。
本発明の複素環化合物とメチルマグネシウムクロリドとを溶媒の存在下で撹拌すると、該複素環化合物中のハロゲン原子(X又はY)のどちらかが選択的に反応するので、その反応液に適切な触媒(例えば、塩化1,3−ジフェニルホスフィノプロパンニッケル(II)(Ni(dppp)Cl2)等)を加えることで重合が起こり、HTレジオレギュラーポリマーが得られる。また、このような反応性(選択性)の違いを利用して、前記複素環化合物を基質とした位置異性体の一種のみを選択的に得ることができる。
(i)2-ブロモ-4-ヘキシルチアゾールの合成
2-アミノ-4-ヘキシルチアゾール(Helvetica Chemica Acta XXXII, Fasciculus I, 35 (1949) 10.0 g(54.3 mmol)を溶解させたアセトニトリル40mLに、亜硝酸t-ブチル8.39 mL(70.5 mmol)を加え、臭化銅(II)12.1 g(54.3 mmol)のアセトニトリル20mL懸濁液をアルゴンガス雰囲気下で氷冷しながら少量ずつ加えて2時間撹拌した。次いで、得られた反応混合液をクロロホルム/ヘキサン混合液100 mlに注ぎ、沈殿物をろ過で取り除いた。ろ液を20重量%塩酸水溶液 100 mlで3回洗浄した後、クロロホルムで抽出を行った。得られた抽出液を無水硫酸マグネシウムで乾燥させた後、減圧下で濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒:クロロホルム/ヘキサン=1/1(容積比))により精製を行った。マススペクトルに臭素原子を一個含有する分子量248のピークが認められたことから、目的とする2-ブロモ-4-ヘキシルチアゾールが得られたことが確認できた。
2-ブロモ-4-ヘキシルチアゾール 4.07 g(16.4 mmol)をアセトニトリル8mLに溶解させ、N−ヨードスクシンイミド4.41 g (19.7 mmol)のアセトニトリル32mL溶液をアルゴンガス雰囲気下で加えて18時間還流した。次いで、得られた反応混合液をNa2S2O3水溶液で洗浄し、水層はクロロホルムで抽出し、有機層に加えた。有機層を濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒:クロロホルム/ヘキサン=1/1(容積比))により、赤色透明液体を取り出した。マススペクトルに臭素原子を一個含有する分子量373のピークが認められたことから、前記赤色透明液体は、目的とする2-ブロモ-4-ヘキシル-5-ヨードチアゾールであることが確認できた。その収量は4.80gであり、収率78.3%であった。
(1) 1H-NMR (ppm/300MHz, CDCl3) 0.89 (3H, t), 1.31 (6H, m), 1.66 (2H, m), 2.71 (2H, m)
(2) 13C-NMR (ppm/75MHz, CDCl3) 14.1, 22.6, 28.8, 29.0, 31.4, 31.5, 69.8, 138.9, 161.8
(iii)2-クロロ-4-ヘキシルチアゾールの合成
アセトニトリル200mLに亜硝酸t-ブチル9.7 mL(81 mmol)と塩化銅(II)8.75 g(65.1 mmol)を加え、アルゴンガス雰囲気下で氷冷しながら2-アミノ-4-ヘキシルチアゾール(Helvetica Chemica Acta XXXII, Fasciculus I, 35 (1949) 10.0 g(54.3 mmol)を溶解させたアセトニトリル10mLを少量ずつ加え、室温に戻して2時間撹拌した。次いで、得られた反応混合液をクロロホルム/ヘキサン混合液100 mlに注ぎ、沈殿物をろ過で取り除いた。ろ液を20重量%塩酸水溶液 100 mlで3回洗浄した後、クロロホルムで抽出を行った。得られた抽出液を無水硫酸マグネシウムで乾燥させた後、減圧下で濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒:クロロホルム/ヘキサン=1/1(容積比))により精製を行うことで、目的とする2-クロロ-4-ヘキシルチアゾールが得られた。
2-クロロ-4-ヘキシルチアゾール 5.30 g(26.0 mmol)とN−ヨードスクシンイミド7.02 g (31.2 mmol)をアセトニトリル40mLに溶解させ、アルゴンガス置換をして50℃で2時間撹拌した。得られた反応混合液をNa2S2O3水溶液で洗浄し、水層はクロロホルムで抽出し有機層に加えた。有機層を濃縮し、シリカゲルカラムクロマトグラフィー(展開溶媒:クロロホルム/ヘキサン=1/1(容積比))により、赤色透明液体を取り出した。マススペクトル(装置:HP-6890GC/HP-5973MSD、カラム:SGE BPX-5(30m×0.25mm I.D.×0.25μm)、カラム温度:50℃(5分)→10℃/分→350℃(5分 hold)、注入口温度:280℃、キャリアーガス:He、1.0ml/分)に塩素原子を一個含有する分子量330のピークが認められたことから、前記赤色透明液体は、目的とする2-クロロ-4-ヘキシル-5-ヨードチアゾールであることが確認できた。その収量は7.50gであり、収率は87.6%であった。
(1) 1H-NMR (ppm/300MHz, CDCl3) 0.89 (3H, t), 1.31 (6H, m), 1.66 (2H, m), 2.69 (2H, m)
(2) 13C-NMR (ppm/75MHz, CDCl3) 14.0, 22.9, 29.1, 29.2, 31.78, 31.82, 68.4, 154.9, 160.5
(v)HTレジオレギュラーポリチアゾールの合成
アルゴンガス雰囲気下、2-クロロ-4-ヘキシル-5-ヨードチアゾール 1.00g (3.03 mmol)をテトラヒドロフラン(THF) 5mLに溶かし、-78℃に冷却した後、3.0M メチルマグネシウムクロリドTHF溶液 1.01mL(3.03mmol)を滴下し、1時間攪拌して、反応溶液を得た。塩化1,3−ジフェニルホスフィノプロパンニッケル(II)(Ni(dppp)Cl2) 0.082g(0.15mmol)のTHF5mL懸濁液を注加し、0℃で4.5時間撹拌後、メタノール100mL中に反応溶液を滴下したところ、沈殿が析出した。こうして得られた溶液(沈殿含む)を、ろ過、メタノールで洗浄し、得られた沈殿物を減圧乾燥することにより、赤紫色を呈する粉末としてHTレジオレギュラーポリ(4-ヘキシルチアゾール-2,5-ジイル) (HT-PHTz) 328mg(収率:64.7%)を得た。
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JP2007118644A JP5637650B2 (ja) | 2006-11-22 | 2007-04-27 | 複素環化合物 |
PCT/JP2007/072710 WO2008062892A1 (fr) | 2006-11-22 | 2007-11-19 | Composés hétérocycliques et polymères hétérocycliques |
EP07832435A EP2128146A4 (en) | 2006-11-22 | 2007-11-19 | HETEROCYCLIC COMPOUNDS AND HETEROCYCLIC POLYMERS |
KR1020097012766A KR20090080566A (ko) | 2006-11-22 | 2007-11-19 | 복소환 화합물 및 복소환 중합체 |
US12/515,436 US20090318651A1 (en) | 2006-11-22 | 2007-11-19 | Heterocyclic compound and heterocyclic polymers |
US14/102,800 US8940856B2 (en) | 2006-11-22 | 2013-12-11 | Heterocyclic compound and heterocyclic polymers |
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EP2128146A1 (en) | 2009-12-02 |
US20140100352A1 (en) | 2014-04-10 |
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WO2008062892A1 (fr) | 2008-05-29 |
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