Pomeranz-Fritsch反応による1-置換イソキノリン誘導体および1,4-Benzoxazepine関連化合物の合成について : 複素環式化合物の合成研究 第320報

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  • Syntheses of 1-Substituted Isoquinoline and 1, 4-Benzoxazepine Derivatives by Pomeranz-Fritsch Reaction : Studies on the Syntheses of Heterocyclic Compounds. CCCXX

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説明

Since the compound (VI) has been well known as a peripheral vasodilator agent, synthesis of its benz [e] [1, 4] oxazepine derivatives was carried out in order to examine their activities. Furthermore, 1-benzylisoquinoline derivatives as well as 1, 4-benzoxazepine derivatives had not yet been obtained by Pomeranz-Fritsch reaction with sulfuric acid as condensing reagent. We now have established that 1-benzylisoquinolines (XXV, XXVI, XXVII and XXVIII) as by-products and benz [e] [1, 4] oxazepine derivatives (XXIX, XXX, XXXI and XXXII) can be obtained by Pomeranz-Fritsch reaction with polyphosphoric acid. In addition, cyclization of XXXIV with polyphosphoric acid gave debrominated 1-benzylisoquinoline (II) together with 1, 4-benzoxazepine derivative (XXXV). Although cyclization of XXXVI and XXXVII afforded 1-benzylisoquinoline derivatives (XXXVIII and XL), the expected 1, 4-benzoxazepine derivatives (XLI and XLII) were not obtained in both cases.

収録刊行物

  • 薬学雑誌

    薬学雑誌 89 (8), 1048-1055, 1969

    公益社団法人 日本薬学会

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