[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.
A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives. -The approach includes the Mumm reaction of imidoyl chlorides with α-amino acids followed by reductive cyclization as key steps. -(ZHICHKIN*, P.; KESICKI, E.; TREIBERG, J.; BOURDON, L.; RONSHEIM, M.; OOI, H. C.; WHITE, S.; JUDKINS, A.; FAIRFAX, D.; Org. Lett. 9 (2007) 7, 1415-1418; Albany Mol. Res., Inc., Albany, NY 12212, USA; Eng.) -R. Steudel 33-147
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