Scholarlink

Abstract <p>The alkylation of dimethyl acetonedicarboxylate with halogen derivatives in the presence of potassium carbonate in dimethyl sulfoxide at 60–70°C led to the formation of C- and O-alkylation products. The <i>O</i>-alkyl derivatives rearranged to the corresponding <i>C</i>-alkyl isomer on heating above 180°C. The reactions of the title compound with ethyl 2-bromopropanoate and 1,3-dichloroacetone under similar conditions involved both methylene groups of the substrate. The product of O-alkylation of dimethyl acetonedicarboxylate with bromoacetaldehyde diethyl acetal is stable up to 200°C; however, hydrolysis of the acetal moiety gave the corresponding aldehyde which isomerized to <i>C</i>-(2-oxoethyl) derivative, followed by intramolecular cyclization to substituted furan. The reaction of dimethyl acetonedicarboxylate with chloroacetonitrile produced <i>C</i>-(cyano­methyl) derivative which cyclized to α-aminofuran in acidic medium.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Alkylation of Dimethyl Acetonedicarboxylate with Halogen Compounds

  • 期刊论文

  • 发表日期：

    2025年9月1日

查看全文
  • V. M. Ismailov,
  • I. A. Mamedov,
  • R. A. Gasymov,
  • N. N. Yusubov

摘要

Abstract

The alkylation of dimethyl acetonedicarboxylate with halogen derivatives in the presence of potassium carbonate in dimethyl sulfoxide at 60–70°C led to the formation of C- and O-alkylation products. The O-alkyl derivatives rearranged to the corresponding C-alkyl isomer on heating above 180°C. The reactions of the title compound with ethyl 2-bromopropanoate and 1,3-dichloroacetone under similar conditions involved both methylene groups of the substrate. The product of O-alkylation of dimethyl acetonedicarboxylate with bromoacetaldehyde diethyl acetal is stable up to 200°C; however, hydrolysis of the acetal moiety gave the corresponding aldehyde which isomerized to C-(2-oxoethyl) derivative, followed by intramolecular cyclization to substituted furan. The reaction of dimethyl acetonedicarboxylate with chloroacetonitrile produced C-(cyano­methyl) derivative which cyclized to α-aminofuran in acidic medium.