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An efficient and straightforward one-step access to 1,3,5-trisubstituted 5’-hydroxyimidazolidine-2,4-diones (hydantoins) is described. Under simple heating, this reaction proceeded through a sequential condensation/intramolecular nucleophilic addition/O → N acyl migration between α-keto acids and carbodiimides. A series of 1,3,5-trisubstituted 5’-hydroxyhydantoins, including protected polyandrocarpamide D analogues, has been successfully synthesized in moderate to excellent yields.

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Versatile Access to 1,3,5-Trisubstituted 5’-Hydroxyimidazolidine-2,4-diones (Hydantoins) from α-Keto Acids and Carbodiimides: Towards the Synthesis of Marine Thermochromic Polyandrocarpamide D

  • 会议论文

  • 发表日期：

    2025年

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  • Yudhi Dwi Kurniawan,
  • Patrick Perlmutter

摘要

An efficient and straightforward one-step access to 1,3,5-trisubstituted 5’-hydroxyimidazolidine-2,4-diones (hydantoins) is described. Under simple heating, this reaction proceeded through a sequential condensation/intramolecular nucleophilic addition/O → N acyl migration between α-keto acids and carbodiimides. A series of 1,3,5-trisubstituted 5’-hydroxyhydantoins, including protected polyandrocarpamide D analogues, has been successfully synthesized in moderate to excellent yields.