Synthesis of the Erythrinan Skeleton by Acid-Promoted Cyclization of N-(3-Oxo-1-cyclohexen-1-yl)-N-[2-(3,4-dimethoxyphenyl) ethyl]-α-(methylsulfinyl) acetamide

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概要

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• Heating of the N-(3-oxo-1-cyclohexene-1-yl)-α-(methylsulfinyl) acetamides 7a-c with p-toluenesulfonic acid in 1,2-dichloroethane gave the 3,5,6,7-tetrahydro-3-methylthio-1H-indole-2,4-diones 9a-c. Compound 9b, when heated in 85% phosphoric acid at 80℃, underwent further cyclization to afford the 7-(methylthio) erythrinan-1,8-dione 14 and the 6,7-didehydroerythrinan-1,8-dione 15 in 53 and 15% yields, respectively. Refluxing of 9b in 99% formic acid gave 15 in 43% yield. Double cyclization of 7b to 14 and 15 was achieved by refluxing in 99% formic acid in 7 and 47% yields, respectively. In marked contrast, treatment of 9c with formic acid resulted in the formation of the 1,3-dihydro-4-hydroxy-2-methylthio-2H-indol-2-one 16 and the 3,5,6,7-tetrahydro-1H-indole-2,4-dione 17 in 47 and 16% yields, respectively.

• 社団法人日本薬学会の論文
• 1985-12-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• 池田 正澄

  Kyoto Pharmaceutical University

• 石橋 弘行

  Kyoto Pharmaceutical University

• 赤井 周司

  大阪大学大学院薬学研究科

• 赤井 周司

  Faculty of Pharmaceutical Sciences, Osaka University

• 原田 鈴美

  Kyoto Pharmaceutical University

• 佐藤 佳寿美

  Kyoto Pharmaceutical University

• 石橋 弘行

  金沢大学薬学部

• 石橋 弘行

  京都薬科大学

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