Scholarlink

Abstract <p>Methods for the synthesis of 5-(adamantan-1-yl)furan-2- and -3-carboxylic acids were developed. Phosphorylation of the acid chlorides of these acids with triethyl phosphite yielded stable furoylphosphonates, which then reacted with ethoxycarbonylmethylenetriphenylphosphorane to form 3-[(5-adamantan-1-yl)furanyl]-3-(diethoxyphosphoryl)acrylates. Bromination of the methyl group of these compounds with <i>N</i>-bromosuccinimide provided bromomethyl and dibromomethyl derivatives. The latter were converted under mild conditions to the corresponding aldehydes, which in turn reacted with hydrazine to give adamantylated derivatives of dihydrofuro[2,3-<i>d</i>][1,2]diazepine. Further treatment of bromomethyl derivative with thiourea and subsequent hydrolysis of the resulting thiouronium salt led to the formation of 4,7-dihydro-5<i>H</i>-thiopyrano[3,4-<i>b</i>]furan containing an adamantyl moiety.</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

Adamantylfuroylphosphonates: Synthesis and Further Transformations

  • 期刊论文

  • 发表日期：

    2025年5月21日

查看全文
  • L. M. Pevzner,
  • M. L. Petrov,
  • A. V. Stepakov

摘要

Abstract

Methods for the synthesis of 5-(adamantan-1-yl)furan-2- and -3-carboxylic acids were developed. Phosphorylation of the acid chlorides of these acids with triethyl phosphite yielded stable furoylphosphonates, which then reacted with ethoxycarbonylmethylenetriphenylphosphorane to form 3-[(5-adamantan-1-yl)furanyl]-3-(diethoxyphosphoryl)acrylates. Bromination of the methyl group of these compounds with N-bromosuccinimide provided bromomethyl and dibromomethyl derivatives. The latter were converted under mild conditions to the corresponding aldehydes, which in turn reacted with hydrazine to give adamantylated derivatives of dihydrofuro[2,3-d][1,2]diazepine. Further treatment of bromomethyl derivative with thiourea and subsequent hydrolysis of the resulting thiouronium salt led to the formation of 4,7-dihydro-5H-thiopyrano[3,4-b]furan containing an adamantyl moiety.