Studies on Tetrahydroisoquinolines. I. Formation and Acid-Catalyzed Rearrangement of 10-Acetoxy-6-methoxy-2-methyl-7-oxo-Δ^<5,6,8,9>-hexahydroisoquinolines

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概要

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• Treatment of 7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolines (IXa-d) with lead tetraacetate was found to give the corresponding p-quinol acetates (XIa-d) irrespective of the absence or the presence of substituent at 1-position. Reaction of XIa-d under Thiele condition (Ac_2O-conc. H_2SO_4) afforded the corresponding 4,7-diacetates (XIIIa-d), in which one of newly introduced acetoxy groups was not at 5- but 4-position. 4-Hydroxy compound (XV) was also synthesized by application of Pomeranz-Fritsh type reaction to N-formyl-N-veratrylglycine (XIX). The present rearrangement was infered to proceed through p-quinone methide (XXV-II) as an intermediate.

• 公益社団法人日本薬学会の論文
• 1971-10-25

著者

• 井上 哲也

  Faculty Of Pharmaceutical Sciences Osaka University

• 梅沢 文輔

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 大山 恵子

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 井上 勗

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd.

• Inoue T

  Ohmiya Research Laboratory Fuji Yakuhin Co. Ltd

• 利岡 佶

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 梅澤 文輔

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 梅沢 文輔

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 寺山 泰郎

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 井上 勗

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• 寺山 泰郎

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo:(present Address)the Lion Dentifrice

• Inoue T

  Osaka University Of Pharmaceutical Sciences

• 井上 輝比古

  Pharmaceutical Research Department Ube Laboratory Corporate Research & Development Ube Industrie

• 星野 修

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• 大山 恵子

  Faculty Of Pharmaceutical Sciences Science University Of Tokyo

• Inoue Takao

  Faculty Of Pharmaceutical Sciences Hoshi University

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