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Abstract <p>The reaction of 3-amino-4-aryl-2-acyl-6-phenylthieno[2,3-<i>b</i>]pyridines with chloroacetyl chloride in toluene yielded the corresponding chloroacetamides. The latter underwent a cascade rearrangement upon treatment with KSCN in an acetone–EtOH mixture to form previously undescribed ethyl esters of (pyrido[3′,2′:4,5]thieno[3,2-<i>d</i>]pyrimidin-2-ylthio)acetic acids. Under similar conditions, 4-(4-methoxyphenyl)-6-phenyl-3-(chloroacetamido)thieno[2,3-<i>b</i>]pyridine-2-carbonitrile produced only the isomerization product of the intermediately formed thiocyanatoacetamide—3-(2-imino-4-oxothiazolidin-3-yl)-4-(4-methoxyphenyl)-6-phenylthieno[2,3-<i>b</i>]pyridine-2-carbonitrile.</p>

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Synthesis of (Pyrido[3ʹ,2ʹ:4,5]thieno[3,2-d]pyrimidin-2-ylthio)acetic Acids Esters by the Reaction of N-(Thieno[2,3-b]pyridin-3-yl)-α-chloroacetamides with Potassium Thiocyanate

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • S. V. Rudenko,
  • D. Yu. Lukina,
  • P. S. Kuchmas,
  • V. K. Kindop,
  • A. V. Bespalov,
  • V. V. Dotsenko,
  • N. A. Aksenov,
  • I. V. Aksenova

摘要

Abstract

The reaction of 3-amino-4-aryl-2-acyl-6-phenylthieno[2,3-b]pyridines with chloroacetyl chloride in toluene yielded the corresponding chloroacetamides. The latter underwent a cascade rearrangement upon treatment with KSCN in an acetone–EtOH mixture to form previously undescribed ethyl esters of (pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-2-ylthio)acetic acids. Under similar conditions, 4-(4-methoxyphenyl)-6-phenyl-3-(chloroacetamido)thieno[2,3-b]pyridine-2-carbonitrile produced only the isomerization product of the intermediately formed thiocyanatoacetamide—3-(2-imino-4-oxothiazolidin-3-yl)-4-(4-methoxyphenyl)-6-phenylthieno[2,3-b]pyridine-2-carbonitrile.