The pyroglutamate hydantoin rearrangement

Nicolai Dieltiens, Diederica D. Claeys, Viktor Zhdankin, Victor N. Nemykin, Bart Allaert, Francis Verpoort, Christian V. Stevens

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


When a mixture of a pyroglutamate and an isocyanate in THF is treated with NaH, a ring transformation occurs leading to functionalised hydantoins. The novel reaction involves a ring-closing ring-opening sequence providing a new and straightforward access to an interesting class of heterocyclic compounds. Furthermore, starting from pyroglutamates allows the synthesis of highly substituted hydantoins under very mild conditions. This ring transformation in combination with ring-closing metathesis is used in a four-step reaction sequence for the synthesis of multi-functionalised bicyclic hydantoin derivatives.

Original languageEnglish (US)
Pages (from-to)2649-2660
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number11
StatePublished - May 26 2006


  • Fused-ring systems
  • Hydantoins
  • Isocyanates
  • Lactams
  • Nitrogen heterocycles
  • Pyroglutamates
  • Rearrangement
  • Ring-closing metathesis


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