The Reactions of Activated Amides. VI. The Reactions of 1-Methyl-2-pyrrolidone Dimethylacetal and 2-Methylmercapto-1-methyl-2-pyrroline with Dimethyl Acetylenedicarboxylate

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概要

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• The reaction of 1-methyl-2-pyrrolidone dimethylacetal (IV) with dimethyl acetylenedicarboxylate (I) was carried out expecting the formation of the simple dihydroazepine derivative. However, the products actually obtained were the indoline derivative (VI), the isomeric pyrrolidone derivatives (VII and VIII) and the tetracarbomethoxy-1,3-butenyl pyrroline derivative (IX) when dioxane was used as the solvent, while the 1 : 1 adduct (X) was found to be the main product when the reaction was carried out in benzene. On the other hand, when 1-methyl-2-methylmercapto-2-pyrroline (XIII) was employed, the desired product (XIV) was obtained as a main product along with VI, VII, the Diels-Alder adduct (XV), and dimethyl 2,3-bis-methylmercaptosuccinate (XVI).

• 公益社団法人日本薬学会の論文
• 1972-08-25

著者

• 伴 義雄

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University

• 大石 武

  Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy

• 伴 義雄

  東邦大・薬

• 伴 義雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 大石 武

  北大・薬:(現)理化学研究所

• 村上 信二

  Faculty Of Pharmaceutical Sciences Hokkaido University

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