A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives

Org Lett. 2007 Mar 29;9(7):1415-8. doi: 10.1021/ol070276c. Epub 2007 Mar 10.

Abstract

[structure: see text]. An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee >93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyclization
  • Molecular Structure
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Stereoisomerism

Substances

  • Quinazolinones