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<p>An efficient, four-component strategy for the synthesis of multifunctionalized thiazole-fused indole derivatives under mild conditions has been established. The acid-catalyzed four-component cascade reactions were conducted by reacting inexpensive and readily available 2-methylbenzo[<i>d</i>]thiazol-5/6-amine, 2,2-dihydroxy-1-arylethan-1-one, Meldrum’s acid, and alcohol or amine in refluxing acetonitrile. A total of 30 examples were studied, and the results revealed a broad substrate scope and moderate to good yields (42–76%). A reaction mechanism involving Knoevenagel condensation, Michael addition, enamine-imine transformation, and amine hydrolysis of esters has been proposed to explain the transformation processes. The advantages of the present strategy include an effective one-pot four-component strategy, mild reaction conditions, structurally diverse thiazole-fused indole derivatives, and the absence of metal promoters.</p> Graphical abstract <p></p>

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Synthesis of structurally diverse thiazole-fused indole derivatives via a one-pot four-component cascade reaction

  • 期刊论文

  • 发表日期：

    2026年4月26日

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  • Guanghua Wei,
  • Qi Zhang,
  • Chunmei Li,
  • Furen Zhang

摘要

An efficient, four-component strategy for the synthesis of multifunctionalized thiazole-fused indole derivatives under mild conditions has been established. The acid-catalyzed four-component cascade reactions were conducted by reacting inexpensive and readily available 2-methylbenzo[d]thiazol-5/6-amine, 2,2-dihydroxy-1-arylethan-1-one, Meldrum’s acid, and alcohol or amine in refluxing acetonitrile. A total of 30 examples were studied, and the results revealed a broad substrate scope and moderate to good yields (42–76%). A reaction mechanism involving Knoevenagel condensation, Michael addition, enamine-imine transformation, and amine hydrolysis of esters has been proposed to explain the transformation processes. The advantages of the present strategy include an effective one-pot four-component strategy, mild reaction conditions, structurally diverse thiazole-fused indole derivatives, and the absence of metal promoters.

Graphical abstract