JPS58152864A - エナミン並びにエナミンの製造方法 - Google Patents

エナミン並びにエナミンの製造方法

Info

Publication number: JPS58152864A
Authority: JP; Japan
Prior art keywords: group; general formula; alkyl; aryl; compound
Prior art date: 1982-02-17
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.): Granted

Application number

JP2224983A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0463062B2 (2

Inventor

ベルナルド・ル−カス・フエリンガ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

Priority date (The priority date 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 date listed.)

1982-02-17

Filing date

1983-02-15

Publication date

1983-09-10

1983-02-15 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1983-09-10 Publication of JPS58152864A publication Critical patent/JPS58152864A/ja

1992-10-08 Publication of JPH0463062B2 publication Critical patent/JPH0463062B2/ja

Status Granted legal-status Critical Current

Links

150000002081 enamines Chemical class 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title description 13
150000001875 compounds Chemical class 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 27
238000000034 method Methods 0.000 claims description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 17
125000002877 alkyl aryl group Chemical group 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 16
239000003638 chemical reducing agent Substances 0.000 claims description 14
-1 lithium aluminum hydride Chemical compound 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
150000004678 hydrides Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000012280 lithium aluminium hydride Substances 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 9
239000012044 organic layer Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BCKZBECRNOYQLR-UHFFFAOYSA-N S(=O)(=O)=C=CN Chemical class S(=O)(=O)=C=CN BCKZBECRNOYQLR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
235000005513 chalcones Nutrition 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
CVPNVSHNHQJGLP-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-2-phenylacetonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C#N)C1=CC=CC=C1 CVPNVSHNHQJGLP-UHFFFAOYSA-N 0.000 description 1
BBNNLJMGPASZPD-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonylacetonitrile Chemical compound CC1=CC=C(S(=O)(=O)CC#N)C=C1 BBNNLJMGPASZPD-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
NIFXBVZGPWTQJS-UHFFFAOYSA-N C(C)[AlH]CC.[Li] Chemical compound C(C)[AlH]CC.[Li] NIFXBVZGPWTQJS-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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 1
239000012448 Lithium borohydride Substances 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical class [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
ZYLUDZJMFPIZGW-UHFFFAOYSA-N n-ethenyl-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NC=C)C=C1 ZYLUDZJMFPIZGW-UHFFFAOYSA-N 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000010287 polarization Effects 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
102220007331 rs111033633 Human genes 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP2224983A 1982-02-17 1983-02-15 エナミン並びにエナミンの製造方法 Granted JPS58152864A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8204595		1982-02-17
GB8204595		1982-02-17

Publications (2)

Publication Number	Publication Date
JPS58152864A true JPS58152864A (ja)	1983-09-10
JPH0463062B2 JPH0463062B2 (2)	1992-10-08

Family

ID=10528390

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2224983A Granted JPS58152864A (ja)	1982-02-17	1983-02-15	エナミン並びにエナミンの製造方法

Country Status (4)

Country	Link
EP (1)	EP0086510B1 (2)
JP (1)	JPS58152864A (2)
CA (1)	CA1226869A (2)
DE (1)	DE3361186D1 (2)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2959617A (en) *	1957-03-04	1960-11-08	Du Pont	Synthesis of vinyl amines
DE2639498A1 (de) *	1976-09-02	1978-03-09	Bayer Ag	Neue schwefelhaltige amino-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

1983
- 1983-01-14 DE DE8383200055T patent/DE3361186D1/de not_active Expired
- 1983-01-14 EP EP19830200055 patent/EP0086510B1/en not_active Expired
- 1983-02-15 CA CA000421645A patent/CA1226869A/en not_active Expired
- 1983-02-15 JP JP2224983A patent/JPS58152864A/ja active Granted

Also Published As

Publication number	Publication date
EP0086510A2 (en)	1983-08-24
DE3361186D1 (en)	1985-12-19
CA1226869A (en)	1987-09-15
EP0086510A3 (en)	1983-12-07
JPH0463062B2 (2)	1992-10-08
EP0086510B1 (en)	1985-11-13

Publication	Publication Date	Title
JPS63295520A (ja)	1988-12-01	非対称なビフェニル誘導体の製造法
JPS58152864A (ja)	1983-09-10	エナミン並びにエナミンの製造方法
JPS5811867B2 (ja)	1983-03-04	５，５−ジメチル−４−フエニルオキサゾリジン−２−オン誘導体の製造方法
JP2554883B2 (ja)	1996-11-20	新規アゾアミジン化合物及びその塩
JPH05508633A (ja)	1993-12-02	デフェロキサミンの調製に用いる中間体
JP3959178B2 (ja)	2007-08-15	ヒドラジン誘導体の製造方法、その中間体および中間体の製造方法
CA1208233A (en)	1986-07-22	Intermediates for the preparation of 4-phenyl-1,3- benzodiazepins and methods for preparing the intermediates
JPS6045179B2 (ja)	1985-10-08	新規環状アミノアルコ−ル類およびその製造法
JPS58216153A (ja)	1983-12-15	チオビスフエノ−ル類の製造方法
JPS5844650B2 (ja)	1983-10-04	５−オキソカルボン酸の製法
SU858560A3 (ru)	1981-08-23	Способ получени N-карбамоилэтилоксанилата
JPS5812273B2 (ja)	1983-03-07	シンキアセチレンアルコ−ルユウドウタイノシンキセイゾウホウ
JPS58201757A (ja)	1983-11-24	アゾキシ化合物及びアゾ化合物の製造方法
JPS5934718B2 (ja)	1984-08-24	エチルアセチレンマグネシウムハクイドの製造方法
JPS60120844A (ja)	1985-06-28	９−カルバモイルフルオレン誘導体の製法
JPS6399041A (ja)	1988-04-30	光学活性アミン類の製造方法
CA1074305A (en)	1980-03-25	Amino-substituted tetracyclic compounds
JPS5858335B2 (ja)	1983-12-24	アルフア − チカンアセトンノセイゾウホウ
JPS58154563A (ja)	1983-09-14	新規ベンゾオキサジンの製造方法
JPH023672A (ja)	1990-01-09	２，６‐ジエチルアニリン誘導体およびその製法
JPS60190761A (ja)	1985-09-28	４−アミノインド−ルの製造方法
JPH0460471B2 (2)	1992-09-28
JPH01313471A (ja)	1989-12-18	Ｎ−スルフアモイルアミジン化合物の製造法
JPS61291566A (ja)	1986-12-22	複素芳香族グリオギザル酸ハロゲニドの製造方法
JPS61130299A (ja)	1986-06-18	５−フルオロシチシン化合物塩酸塩の製法