Thermal Elimination of Carbonyl Sulfide from O-Aryl Thionocarbonates of Pyrrolidine-, Piperidine-, and Tetrahydrothiophene-2-ethanol

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概要

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• Pyrolysis of O-2-(1-benzyl-2-pyrrolidinyl and 2-piperidyl)ethyl O-phenyl thionocarbonates (4 and 25) in acetonitrile gave 1-benzyl-4-phenoxyhexahydro-1H-azepine (7) and 1-benzyl-4-phenoxyoctahydroazocine (26) with liberation of COS in 55% and 32% yields, accompanied with 2-(2-phenoxyethyl)pyrrolidine and piperidine (8 and 27), via the azetidinum intermediate (6). On the other hand, O-phenyl O-2-(2-tetrahydrothienyl)ethyl thionocarbonate (32) resulted in the predominant formation of the O, S-rearrangement product (35) in 53% yield.

• 社団法人日本薬学会の論文
• 1990-11-25

著者

• 山崎 直樹

  Osaka University Of Pharmaceutical Sciences

• 春沢 信哉

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Osaka University of Pharmaceutical Sciences

• 坂之上 里美

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  大阪薬科大学

• 米田 龍司

  Agroscience Research Laboratories Sankyo Co. Ltd.

• 栗原 拓史

  Osaka College Of Pharmacy

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