Straightforward ring expansion of pyroglutamates to perhydro-1,3-diazepine-2,4-diones

Org Lett. 2005 Mar 17;7(6):1117-9. doi: 10.1021/ol050050e.

Abstract

[reaction: see text] Perhydro-1,3-diazepine-2,4-diones are rare and can only be prepared, up to now, by special methods. A new one-step protocol was developed, comprising N-carbamoylation using an isocyanate followed by intramolecular ring expansion. This new methodology provides a straightforward access to this interesting seven-membered skeleton.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azepines / chemical synthesis*
  • Combinatorial Chemistry Techniques*
  • Isothiocyanates / chemistry
  • Molecular Structure
  • Pyrrolidonecarboxylic Acid / chemistry*

Substances

  • Azepines
  • Isothiocyanates
  • isothiocyanic acid
  • Pyrrolidonecarboxylic Acid