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<p>A highly efficient synthesis of some novel series of 3-hydroxy indoles derivatives (3a-j) has been achieved via aldol reaction of 2-amino-4-(ethoxycarbonylmethyl) thiazole with 1&#xa0;H-indol-2,3-diones in presence of water. However the reaction of aldehydes / ketone and primary amines, are generally straight forward and give the expected imines. But here, anomalous behavior was observed as nucleophilic 5-C atom of 2-aminothizole reacts regioselectively with carbonyl group of isatin and gave 3-hydroxy indoles. The finding demonstrates significant product yields of 3-hydroxy indoles, which are highly beneficial building blocks for the synthesis of bioactive alkaloid natural products and drug molecules. The framework of the final compounds have elucidated by detailed spectral and elemental data.</p>

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A Regioselective Synthesis of 3-Hydroxyindoles Via an Intermolecular C (sp2)-C (sp2) Bond Formation

  • 期刊论文

  • 发表日期：

    2025年4月3日

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  • Lata Vodwal,
  • Haritma Chopra,
  • P. Bajaj Gandhi,
  • Chandra Mohan,
  • Arti Jain

摘要

A highly efficient synthesis of some novel series of 3-hydroxy indoles derivatives (3a-j) has been achieved via aldol reaction of 2-amino-4-(ethoxycarbonylmethyl) thiazole with 1 H-indol-2,3-diones in presence of water. However the reaction of aldehydes / ketone and primary amines, are generally straight forward and give the expected imines. But here, anomalous behavior was observed as nucleophilic 5-C atom of 2-aminothizole reacts regioselectively with carbonyl group of isatin and gave 3-hydroxy indoles. The finding demonstrates significant product yields of 3-hydroxy indoles, which are highly beneficial building blocks for the synthesis of bioactive alkaloid natural products and drug molecules. The framework of the final compounds have elucidated by detailed spectral and elemental data.