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Journal of The Chemical Society-perkin Transactions 1 | 1974

Studies on the syntheses of heterocyclic compounds. Part DLXXVII. Synthesis of 2,3,4,5-tetrahydro-1H-benzazepine derivatives by phenolic cyclisation

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru; Seiji Haga

Die aus 3-Benzyloxy-benzaldehyd und Cyanessigsaure in Benzol/NH4-acetat zugangliche Saure (I) wird zu dem Nitril (II) decarboxyliert, dessen Hydrierung am Raney-Ni unter Hochdruck das Amin (III) gibt.


Journal of The Chemical Society-perkin Transactions 1 | 1973

Studies on the syntheses of heterocyclic compounds. Part DII. Synthesis of 1-substituted 1,2,3,4-tetrahydrophthalazines by a pictet–spengler-type reaction of 3-hydroxybenzylhydrazine with carbonyl compounds

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru; T. Uryu; Seiji Haga

Condensations of 3-hydroxybenzylhydrazine with acetone, ethyl methyl ketone, diethyl ketone, cyclohexanone, and 1-methyl-4-piperidone in the presence of acid gave the 1,1-disubstituted 1,2,3,4-tetrahydrophthalazines (2)–(6). On the other hand, the reactions of 3-hydroxybenzoylhydrazine (7) with acetone, cyclohexanone, and benzalde-hyde gave the Schiffs bases (8)–(10).


Journal of Heterocyclic Chemistry | 1978

Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid. [Studies on the syntheses of heterocyclic compounds. Part 742]†‡

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru; Seiji Haga; Keiko Shirayama


Journal of Heterocyclic Chemistry | 1970

Studies on the syntheses of heterocyclic compounds. Part CCCXXIX. Syntheses of i-spiroisoquinoline derivatives by phenolic cyclization†

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru


Chemical & Pharmaceutical Bulletin | 1971

Phenolic Cyclization. IX. Syntheses of Benz [c] phenanthridine and Related Compounds

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; O. Kusama; Emiko Hayashi; Haruhide Ishimaru


Chemical & Pharmaceutical Bulletin | 1969

Phenolic Cyclization. IV. The Mechanism of the Isoquinoline Formation (Studies on the Syntheses of Heterocyclic Compounds. CCCXXXVII)

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru


Chemical & Pharmaceutical Bulletin | 1965

Azabenzomorphane and Related Compounds. II. A Synthesis of 1, 2, 3, 4-Tetrahydro-6H-1, 5-methanobenzo[f][1, 4]diazocine

Tetsuji Kametani; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru


Journal of Heterocyclic Chemistry | 1971

Syntheses of benzomorphan and related compounds. Part III. An alternate synthesis of 3-substituted-1,2,3,4,5,6-hexahydro-8-hydroxy-2,6-methano-6,11-dimethyl-3-benzazocine †‡

Tetsuji Kametani; Kazuo Kigasawa; M. Hayasaka; Kikuo Wakisaka; Fumio Satoh; T. Aoyama; Haruhide Ishimaru


Chemical & Pharmaceutical Bulletin | 1970

Application of Norphenylephrine Derivatives to the Isoquinoline Syntheses : Studies on the Syntheses of Heterocyclic Compounds. CCCLII

Tetsuji Kametani; Fumio Satoh; Hideo Agui; Kyoko Ueki; Kazuo Kigasawa; Mineharu Hiiragi; Haruhide Ishimaru; Shoichiro Horie


Archive | 1977

Preparation of nitriles

Seiji Haga; Mineji Hiiragi; Haruhide Ishimaru; Kazuo Kikazawa; Kikuo Nakazato; Mikio Ouchi; Keiko Shiroyama

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