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February 2, 2026Organic Letters2 citations

A Three-Layer Transformation Strategy toward Functionalized Fused Hydantoins and Diketopiperazines

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MGMaria-Aikaterini GiannakakiMZMarios ZingiridisKFKonstantinos G. Froudas

Key Points

  • The aim is to develop a rapid and scalable synthesis method for thiazolo hydantoins and diketopiperazines.
  • Utilized modified Asinger reaction for initial synthesis from 3-thiazolines
  • Incorporated Ugi-Joullié multicomponent reaction for compound diversification
  • Implemented base-induced annulation for final compound formation
  • Processed on a multigram scale without chromatography
  • Confirmed structures through single-crystal analysis
  • Achieved synthesis of complex compounds in less than 3 hours
  • Enabled telescoped one-pot processing for efficiency
  • Demonstrated a broad substrate scope with late-stage modifications

Abstract

We present mAUCy (modified Asinger-Ugi cyclization), a scalable three-layer strategy enabling rapid synthesis of diverse thiazolo hydantoins and diketopiperazines. Beginning from 3-thiazolines via a modified Asinger reaction, followed by an Ugi-Joullié multicomponent reaction and base-induced annulation, the method delivers complex compounds in less than 3 h. Operable on a multigram scale without chromatography, it allows telescoped one-pot processing, a broad substrate scope, and late-stage modifications. Single-crystal analysis confirmed the scaffold structures.

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Cite This Study

Giannakaki et al. (2026) studied this question.

synapsesocial.com/papers/6980ff08c1c9540dea811b5dhttps://doi.org/10.1021/acs.orglett.5c05391
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