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Abstract <p>A novel methyl 4-(2-chloroethyl)-4<i>H</i>-thieno[3,2-<i>b</i>]pyrrol-5-carboxylate was synthesized by refluxing methyl 4<i>H</i>-thieno[3,2-<i>b</i>]pyrrol-5-carboxylate in 1,2-dichloroethane in the presence of K<sub>2</sub>CO<sub>3</sub>. The acylation of the product with thiophene-2-carbonyl chloride under standard Friedel–Crafts conditions using SnCl<sub>4</sub> yielded the target methyl 4-(2-chloroethyl)- 2-(thiophene-2-carbonyl)-4<i>H</i>-thieno[3,2-<i>b</i>]pyrrole-5-carboxylate. A by-product, 5,6-dihydro-8<i>H</i>-thieno[2′,3′:4,5]pyrrolo[2,1-<i>c</i>][1,4]oxazin-8-one, was also isolated, which was formed by an unusual intramolecular cyclization. The condensation of methyl 4-(2-chloroethyl)-4<i>H</i>-thieno[3,2-<i>b</i>]pyrrol-5-carboxylate with 1<i>H</i>-indole allowed the synthesis of the 2-[(4-ethyl-4<i>H</i>-thieno[3,2-<i>b</i>]pyrrol-5-yl)methyl]-1<i>H</i>-indole.</p>

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Synthesis and Transformations of Methyl 4-(2-chloroethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylate

  • 期刊论文

  • 发表日期：

    2026年1月1日

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  • S. A. Torosyan,
  • Z. F. Nuriakhmetova,
  • M. F. Abdullin,
  • F. A. Gimalova

摘要

Abstract

A novel methyl 4-(2-chloroethyl)-4H-thieno[3,2-b]pyrrol-5-carboxylate was synthesized by refluxing methyl 4H-thieno[3,2-b]pyrrol-5-carboxylate in 1,2-dichloroethane in the presence of K2CO3. The acylation of the product with thiophene-2-carbonyl chloride under standard Friedel–Crafts conditions using SnCl4 yielded the target methyl 4-(2-chloroethyl)- 2-(thiophene-2-carbonyl)-4H-thieno[3,2-b]pyrrole-5-carboxylate. A by-product, 5,6-dihydro-8H-thieno[2′,3′:4,5]pyrrolo[2,1-c][1,4]oxazin-8-one, was also isolated, which was formed by an unusual intramolecular cyclization. The condensation of methyl 4-(2-chloroethyl)-4H-thieno[3,2-b]pyrrol-5-carboxylate with 1H-indole allowed the synthesis of the 2-[(4-ethyl-4H-thieno[3,2-b]pyrrol-5-yl)methyl]-1H-indole.