Abstract

A synthetically simple and convenient approach to tetrasubstituted thiophenes with rare combination of the alkoxy, amino, and cyano groups has been developed. The assembly of polyfunctionalized thiophene ring is implemented in one preparative step by sequential addition of isothiocyanate and 2-bromoacetonitrile to the lithiated (with n-BuLi) alkoxyallene. The reaction proceeds through in situ formation and intramolecular cyclization of cyanomethyl 2-alkoxy-N-buta-2,3-dienimidothioate (1-aza-1,3,4-triene).

A synthetically simple and convenient approach to tetrasubstituted thiophenes with rare combination of the alkoxy, amino, and cyano groups has been developed. The assembly of polyfunctionalized thiophene ring is implemented in one preparative step by sequential addition of isothiocyanate and 2-bromoacetonitrile to the lithiated (with n-BuLi) alkoxyallene. The reaction proceeds through in situ formation and intramolecular cyclization of cyanomethyl 2-alkoxy-N-buta-2,3-dienimidothioate (1-aza-1,3,4-triene).

中文翻译：

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通过锂化烷氧基丙烯与异硫氰酸酯和2-溴乙腈的顺序反应，快速可扩展地无催化剂地合成4-烷氧基-5-氨基-3-甲基噻吩-2-甲腈

摘要

已开发出一种合成简单，方便的方法，以烷氧基，氨基和氰基的罕见组合来合成四取代噻吩。多官能化噻吩环的组装是在一个制备步骤中实现的，方法是将异硫氰酸酯和2-溴乙腈依次添加到锂化的（含n- BuLi）烷氧基丙二烯中。该反应通过氰基甲基2-烷氧基-N -buta-2,3-二亚氨基亚氨基硫酸酯（1-氮杂-1,3,4-三烯）的原位形成和分子内环化而进行。

已开发出一种合成简单，方便的方法，以烷氧基，氨基和氰基的罕见组合来合成四取代噻吩。多官能化噻吩环的组装是在一个制备步骤中实现的，方法是将异硫氰酸酯和2-溴乙腈依次添加到锂化的（含n- BuLi）烷氧基丙二烯中。该反应通过氰基甲基2-烷氧基-N -buta-2,3-二亚氨基亚氨基硫酸酯（1-氮杂-1,3,4-三烯）的原位形成和分子内环化而进行。