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

Maria-Aikaterini Giannakaki1, Marios Zingiridis1, Konstantinos G Froudas1

  • 1Department of Chemistry, University of Crete, Heraklion 700 13, Greece.

Organic Letters
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Summary

We developed a scalable mAUCy strategy for rapid synthesis of thiazolo hydantoins and diketopiperazines. This method efficiently produces complex molecules in under 3 hours, suitable for multigram scales.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Thiazolo hydantoins and diketopiperazines are important heterocyclic scaffolds.
  • Efficient and scalable synthetic routes are needed for these compound classes.

Purpose of the Study:

  • To develop a rapid, scalable, and versatile synthetic strategy for thiazolo hydantoins and diketopiperazines.
  • To enable efficient synthesis of complex heterocyclic compounds.

Main Methods:

  • The mAUCy (modified Asinger-Ugi cyclization) strategy involves three key steps.
  • Utilizes a modified Asinger reaction, an Ugi-Joullié multicomponent reaction, and base-induced annulation.
  • The process is designed for telescoped one-pot processing.

Main Results:

  • The mAUCy strategy enables rapid synthesis of diverse thiazolo hydantoins and diketopiperazines in under 3 hours.
  • The method is scalable to multigram quantities without chromatography.
  • A broad substrate scope and potential for late-stage modifications were demonstrated.

Conclusions:

  • mAUCy provides an efficient and scalable route to complex heterocyclic scaffolds.
  • The strategy facilitates rapid access to diverse thiazolo hydantoins and diketopiperazines.
  • Single-crystal analysis confirmed the structures of the synthesized compounds.