title: A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives.
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.
authors.affiliation: Albany Molecular Research Inc, 21 Corporate Circle, Albany, NY 12212, USA. pavelz@albmolecular.com
authors.forename: Paul
authors.initials: P
authors.lastname: Zhichkin
authors.forename: Edward
authors.initials: E
authors.lastname: Kesicki
authors.forename: Jennifer
authors.initials: J
authors.lastname: Treiberg
authors.forename: Lisa
authors.initials: L
authors.lastname: Bourdon
authors.forename: Matthew
authors.initials: M
authors.lastname: Ronsheim
authors.forename: Hua Chee
authors.initials: HC
authors.lastname: Ooi
authors.forename: Stephen
authors.initials: S
authors.lastname: White
authors.forename: Angela
authors.initials: A
authors.lastname: Judkins
authors.forename: David
authors.initials: D
authors.lastname: Fairfax
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D015394:Molecular Structure; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D052999:Quinazolinones