A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives
journal contributionposted on 29.03.2007, 00:00 by Paul Zhichkin, Edward Kesicki, Jennifer Treiberg, Lisa Bourdon, Matthew Ronsheim, Hua Chee Ooi, Stephen White, Angela Judkins, David Fairfax
An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with α-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.