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Tetsuji Kametani Kazuo Kigasawa Mineharu Hiiragi Haruhide Ishimaru Seiji Haga Keiko Shirayama 《Journal of heterocyclic chemistry》1978,15(3):369-375
2-[4-(1-Oxo-2-isoindolinyl)phenyl]propanoic acid ( 1 ) having a potent analgesic and anti-inflammatory activity could be obtained by three methods, which were found to provide extremely useful ways for the synthesis of 1 from the industrial point of view. (E)- and (Z)-Isomers of 2-butenoic acid and oxiranecarboxylic acid derivatives as the intermedaites in the synthesis of 1 were separated and characterized. Furthermore, the optical resolution of (±)-2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid was successfully achieved using cinchonidine as a resolution reagent. 相似文献
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Tetsuji Kametani Kazuo Kigasawa Tetsutaro Hayasaka Mineharu Hiiragi Haruhide Ishimaru Setsu Asagi 《Journal of heterocyclic chemistry》1966,3(2):129-136
The alkylation of tertiary amines, namely, 2-dimethylaminoethanol, triethylamine, pyridine and isoquinoline with various alkyl carboxylates was investigated. This reaction afforded the corresponding quarternary ammonium salts, e.g., methylation of 2-dimethyl-aminoethanol with methyl salicylate. 相似文献
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Tetsuji Kametani Kazuo Kigasawa Mineharu Hiiragi Kikuo Wakisaka Osamu Kusama Kumeo Kawasaki Hideo Sugi 《Journal of heterocyclic chemistry》1977,14(3):473-475
Synthesis of 1-(2-tetrahydrol'uryl)-5-fluorouracil [Ftorafur] ( 1 ) which is well known as an antitumor agent from 5-fluorouracil ( 2 ) with 2-alkoxytetrahydrofurans (4) is described. Among these reactions, the best yield was obtained by using 2-t-butoxytetrahydrofuran (4h). 相似文献
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Tetsuji Kametani Kazuo Kigasawa Mineharu Hiiragi Fumio Satoh Setsu Saito Hideo Sugi Tsuneo Uryu 《Journal of heterocyclic chemistry》1972,9(5):1057-1059
The configuration of the quaternary ammonium salts (Va and Vb) from 3-benzyl-1,2,3,4,5,6-hexahydro-8-hydroxy-6,11-dimethyl-2,6-methano-3-benzazocine. (II) and 3-methyl-2-butenyl bromide was determined spectroscopically. Moreover, configurational studies on 3-benzyl (VIa and VIb) and 3-(3-methyl-2-butenyl)benzazocinium bromides (VIIa and VIIb) were also achieved. 相似文献
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Phenolic cyclization of 2-(3-hydroxyphenyl)-2-methylethylamine (XIIIa) and 2-(3-hydroxyphenyl)phenethylamine (XIIIb) with various carbonyl compounds afforded eight types of corresponding 1-spirocycloalkano- and 1-spiroheterocycloalkano-1,2,3,4-tetrahydroisoquinoline derivatives (1-VIII) and 1,1-disubstituted-1, 2,3,4-tetrahydroisoquinoline derivative (IX). The acetyl derivatives of VI and IX and the benzoyl derivatives of III and V were also prepared. In addition, a synthetic method for obtaining the starting phenethylamines was examined. 相似文献
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Tetsuji Kametani Kazuo Kigasawa Mincharu Hiiragi Kikuo Wakisaka Nagatoshi Wagatsuma Osamu Kusama Tsunco Urya 《Journal of heterocyclic chemistry》1973,10(6):999-1005
1,2,3,4,5,6-Hexahydro-8-hydroxy-2,6-methano-3,6,1 1-trimethyl-2,3-benzo |g| diazocine (IV) and 1,2,3,4,5,10,11,12-octahydro-7-hydroxy-1,5-dimethylpyridazino |2,3-b| isoquinoline (VI) were synthesized from a common intermediate, 3-(3-methoxyphenyl)-2-butanone (VII), through several steps. Reaction of VII with ethyl bromoacetate gave the mixture of ethyl 4-keto-3-(3-methoxyphenyl)-3-methylpentanoate (XIV) and ethyl 4-keto-5-(3-methoxyphenyl)hexanoate (XV) which were hydrolyzed and condensed with methylhydrazine to give the 4,5-dihydro-5-(3-methoxyphenyl)-2,5,6-trimethyl- (XVIII) and 4,5-dihydro-6-(3-methoxy-α-methylbenzyl)-2-methylpyridazine-3(2H)one (XIX). Reduction of XVIII and XIX followed hy cyclization afforded the 2,3-benzo |g| diazocine (XXII) and the pyridazino |2,3-b| isoquinoline (XXIII) which on treatment with 47% hydrobromine acid afforded the phenolic bases (IV and VI), respectively. The mass spectrum of IV, VI, XXII and XXIII was also discussed. 相似文献