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