Preparation of New Nitrogen-Bridged Heterocycles. 48. Syntheses and Reactions of Ethyl 3-[2-(Methylthio)indolizin-3-yl]acrylate Derivatives

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概要

• 論文の詳細を見る

• Title compounds were prepared in 20-72% yields from the S-aklylation of pyridinium 1- [3-ethoxycarbonyl-1-[(methylthio)thiocarbonyl]]allylides with some alkyl halides, followed by the treatment of the resulting pyridinium salts with a base and then a dehydrogenating agent. In part of these reactions novel heterocycles, ethyl 1-cyano-3-(methylthio)thieno[3,4-b]indolizine-9-carboxylates, were also formed. The oxidation of the title compounds with m-chloroperbenzoic acid gave the corresponding sulfoxides in moderate to good yields, which smoothly underwent Pummerer reactions on treatment with acetic anhydride. The bromination of the 3-vinyl group in the title compounds, followed by treatment of the resulting dibromo adducts with a base afforded ethyl 2-bromo-3-[2-(methylthio)indolizin-3-yl]acrylates, 3-[1-cyano-2-(methylthio)indolizin-3-yl]propiolates, and ethyl thieno[2,3-b]indolizine-2-carboxylate depending upon the substrate used.

• 公益社団法人日本薬学会の論文
• 1999-11-15

著者

• Kakehi Akikazu

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• ITO Suketaka

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• Ito Suketaka

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• SA Hoh

  Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University

• Sa Hoh

  Department Of Chemistry And Material Engineering Faculty Of Engineering Shinshu University

• Ito Suketaka

  Department of Applied Chemistry Faculty of Engineering Nagoya University

関連論文

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