JPH0475228B2 - - Google Patents
Info
- Publication number
- JPH0475228B2 JPH0475228B2 JP4466984A JP4466984A JPH0475228B2 JP H0475228 B2 JPH0475228 B2 JP H0475228B2 JP 4466984 A JP4466984 A JP 4466984A JP 4466984 A JP4466984 A JP 4466984A JP H0475228 B2 JPH0475228 B2 JP H0475228B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrh
- yield
- bipyridine
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001424 substituent group Chemical group 0.000 claims description 19
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000007818 Grignard reagent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000004795 grignard reagents Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- BTZGKPXCNDPTTJ-UHFFFAOYSA-N 2-chloro-6-methylsulfinylpyridine Chemical compound CS(=O)C1=CC=CC(Cl)=N1 BTZGKPXCNDPTTJ-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- -1 N-ethylamino group Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 101150006862 pyrH gene Proteins 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 101000632319 Homo sapiens Septin-7 Proteins 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 102100027981 Septin-7 Human genes 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- YSKBZBQXHPYQMX-UHFFFAOYSA-N 2-pyridin-2-ylsulfinylpyridine Chemical compound C=1C=CC=NC=1S(=O)C1=CC=CC=N1 YSKBZBQXHPYQMX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WYCIUIOCIYSVOZ-UHFFFAOYSA-N 2-chloro-6-(6-chloropyridin-2-yl)pyridine Chemical compound ClC1=CC=CC(C=2N=C(Cl)C=CC=2)=N1 WYCIUIOCIYSVOZ-UHFFFAOYSA-N 0.000 description 3
- KVYNCXZSIHYSDF-UHFFFAOYSA-N 2-chloro-6-methylsulfanylpyridine Chemical compound CSC1=CC=CC(Cl)=N1 KVYNCXZSIHYSDF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 2
- UWYSBYGJIUSXBJ-UHFFFAOYSA-N 2-methylsulfinylpyridine Chemical compound CS(=O)C1=CC=CC=N1 UWYSBYGJIUSXBJ-UHFFFAOYSA-N 0.000 description 2
- LTLAFXLZIOWUQN-UHFFFAOYSA-N 3,5-dichloro-2-methylsulfinylpyridine Chemical compound CS(=O)C1=NC=C(Cl)C=C1Cl LTLAFXLZIOWUQN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- XHXXWWGGXFUMAJ-UHFFFAOYSA-N methanethiol;sodium Chemical compound [Na].SC XHXXWWGGXFUMAJ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VTRRCXRVEQTTOE-UHFFFAOYSA-N 1-methylsulfinylethane Chemical compound CCS(C)=O VTRRCXRVEQTTOE-UHFFFAOYSA-N 0.000 description 1
- KMXGSPJFNYXGGG-UHFFFAOYSA-N 2,6-bis(methylsulfanyl)pyridine Chemical compound CSC1=CC=CC(SC)=N1 KMXGSPJFNYXGGG-UHFFFAOYSA-N 0.000 description 1
- HVTQDSGGHBWVTR-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-phenylmethoxypyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C(C1=CC=CC=C1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CCOCC1 HVTQDSGGHBWVTR-UHFFFAOYSA-N 0.000 description 1
- WZVWSOXTTOJQQQ-UHFFFAOYSA-N 2-bromo-6-(6-bromopyridin-2-yl)pyridine Chemical compound BrC1=CC=CC(C=2N=C(Br)C=CC=2)=N1 WZVWSOXTTOJQQQ-UHFFFAOYSA-N 0.000 description 1
- SOHDPICLICFSOP-UHFFFAOYSA-N 2-bromo-6-methylpyridine Chemical compound CC1=CC=CC(Br)=N1 SOHDPICLICFSOP-UHFFFAOYSA-N 0.000 description 1
- CWFMGEWBDIDVPZ-UHFFFAOYSA-N 2-bromo-6-methylsulfanylpyridine Chemical compound CSC1=CC=CC(Br)=N1 CWFMGEWBDIDVPZ-UHFFFAOYSA-N 0.000 description 1
- ALLSYFVGIGALDA-UHFFFAOYSA-N 2-bromo-6-methylsulfinylpyridine Chemical compound CS(=O)C1=CC=CC(Br)=N1 ALLSYFVGIGALDA-UHFFFAOYSA-N 0.000 description 1
- UNFNHAXJPAFWDP-UHFFFAOYSA-N 2-ethoxy-6-(6-ethoxypyridin-2-yl)pyridine Chemical compound CCOC1=CC=CC(C=2N=C(OCC)C=CC=2)=N1 UNFNHAXJPAFWDP-UHFFFAOYSA-N 0.000 description 1
- FEEZQIITCKKANC-UHFFFAOYSA-N 2-ethoxy-6-methylsulfanylpyridine Chemical compound CCOC1=CC=CC(SC)=N1 FEEZQIITCKKANC-UHFFFAOYSA-N 0.000 description 1
- TYZLDJKRYXLTSQ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methylpyridine Chemical compound CCSC1=CC(C)=CC=N1 TYZLDJKRYXLTSQ-UHFFFAOYSA-N 0.000 description 1
- KWHZBKNQIJMBRV-UHFFFAOYSA-N 2-ethylsulfanyl-6-methylpyridine Chemical compound CCSC1=CC=CC(C)=N1 KWHZBKNQIJMBRV-UHFFFAOYSA-N 0.000 description 1
- OHJPGUSXUGHOGE-UHFFFAOYSA-N 2-methyl-6-(6-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=CC(C=2N=C(C)C=CC=2)=N1 OHJPGUSXUGHOGE-UHFFFAOYSA-N 0.000 description 1
- ZMAGQTSLWCOACC-UHFFFAOYSA-N 2-methylsulfanyl-6-(6-methylsulfanylpyridin-2-yl)pyridine Chemical compound CSC1=CC=CC(C=2N=C(SC)C=CC=2)=N1 ZMAGQTSLWCOACC-UHFFFAOYSA-N 0.000 description 1
- COETZJBDJXXSCZ-UHFFFAOYSA-N 2-methylsulfanyl-6-methylsulfinylpyridine Chemical compound CSC1=CC=CC(S(C)=O)=N1 COETZJBDJXXSCZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DBPSVFRRAOJDIY-UHFFFAOYSA-N 2-sulfinyl-1h-pyridine Chemical class O=S=C1C=CC=CN1 DBPSVFRRAOJDIY-UHFFFAOYSA-N 0.000 description 1
- LBWLQILBBQSTFR-UHFFFAOYSA-N 3,5-dichloro-2-(3,5-dichloropyridin-2-yl)pyridine Chemical compound ClC1=CC(Cl)=CN=C1C1=NC=C(Cl)C=C1Cl LBWLQILBBQSTFR-UHFFFAOYSA-N 0.000 description 1
- WVOLVKSKSYHHIO-UHFFFAOYSA-N 3,5-dichloro-2-methylsulfanylpyridine Chemical compound CSC1=NC=C(Cl)C=C1Cl WVOLVKSKSYHHIO-UHFFFAOYSA-N 0.000 description 1
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
- HYCKHRIFJYTAEM-UHFFFAOYSA-N 5-chloro-2-(5-chloropyridin-2-yl)pyridine Chemical compound N1=CC(Cl)=CC=C1C1=CC=C(Cl)C=N1 HYCKHRIFJYTAEM-UHFFFAOYSA-N 0.000 description 1
- OILZALSAXXKMIK-UHFFFAOYSA-N 5-chloro-2-methylsulfanylpyridine Chemical compound CSC1=CC=C(Cl)C=N1 OILZALSAXXKMIK-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- IQSWKDCJBWGNPD-UHFFFAOYSA-N NSBr Chemical compound NSBr IQSWKDCJBWGNPD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000008111 thiosulfinates Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4466984A JPS60188370A (ja) | 1984-03-08 | 1984-03-08 | ビピリジン誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4466984A JPS60188370A (ja) | 1984-03-08 | 1984-03-08 | ビピリジン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188370A JPS60188370A (ja) | 1985-09-25 |
| JPH0475228B2 true JPH0475228B2 (cs) | 1992-11-30 |
Family
ID=12697849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4466984A Granted JPS60188370A (ja) | 1984-03-08 | 1984-03-08 | ビピリジン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188370A (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1053894C (zh) * | 1996-03-01 | 2000-06-28 | 涿州市桃园农药厂 | 4,4'-联吡啶的制造工艺 |
| US6262273B1 (en) * | 1996-09-12 | 2001-07-17 | Basf Aktiengesellschaft | Substituted thiopyridines |
-
1984
- 1984-03-08 JP JP4466984A patent/JPS60188370A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188370A (ja) | 1985-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bach et al. | Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd (0)-catalyzed cross-coupling | |
| CN110452141B (zh) | 一种无过渡金属催化合成二芳基硫醚类化合物的方法 | |
| CN109879731B (zh) | 一类二芳基甲烷卤代烯烃衍生物及制备方法 | |
| JPH02207083A (ja) | ２―ニトロイミノイミダゾリジン類の製法 | |
| EP1773783B1 (fr) | Procede de preparation de derives n-piperidino-1,5-diphenylpyrazole-3-carboxamide | |
| JPH0475228B2 (cs) | ||
| JP2002173492A (ja) | 軸不斉を有する光学活性な４級アンモニウム塩とそれを用いたβ−ヒドロキシケトンの立体選択的合成 | |
| KR20000051197A (ko) | 술포늄염 및 그 제조방법 | |
| Oae et al. | Ligand exchange and ligand coupling via the σ-sulfurane intermediate in the reaction of alkyl 2-pyridyl sulfoxide with Grignard reagents: convenient preparation of 2, 2′-bipyridines | |
| JP5536458B2 (ja) | ６−ハロゲノ−３−アリールピリジン誘導体の製造方法 | |
| WO2022025117A1 (ja) | フッ素化剤及びフッ素含有化合物の製造方法 | |
| JPS6253970A (ja) | ピラゾ−ル誘導体及びその製法 | |
| US7553924B2 (en) | Catalytic carbon-carbon bond formation | |
| CN115353514B (zh) | 氟代吡啶并嘧啶酮类化合物及其合成方法 | |
| TWI782877B (zh) | 茚并[1,2-b]噁庚因-4-亞基化合物及其製造方法 | |
| US6953871B2 (en) | Processes for producing poly-ethynyl-substituted aromatic compound | |
| CN114085174A (zh) | 一种苄甲基芳基硫醚的一锅法合成方法 | |
| JP4759722B2 (ja) | 置換基を有する芳香族カルボン酸エステルの製造方法 | |
| JP3569877B2 (ja) | ｍ−置換−α−ヒドロキシメチルスチレン誘導体の製造法および３−クロロ−α−ブロモスチレン | |
| JP2558275B2 (ja) | ゲラニルフエニルスルホンの製造方法 | |
| KR101957989B1 (ko) | 유기붕소 촉매를 이용한 안티-(2-알킬)사이클로프로필 실란 화합물의 제조방법 | |
| JP3804080B2 (ja) | トリアリールアミン化合物の製造法 | |
| CN119219536A (zh) | 一种钯催化制备亚磺酰基化合物的方法及其应用 | |
| JP4105482B2 (ja) | トリハロ置換芳香族化合物の製造法 | |
| JPH10130178A (ja) | ｇｅｍ−ジフルオロオレフィン類の製造方法、同製造方法に用いるジルコノセン、及びその製造方法 |