Tetrahedron p. 1295 - 1310 (1990)
Update date:2022-08-05
Topics:
Bergman, Jan
Brynolf, Anna
Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1, using the Mitsunobo reaction, gave (+)-(R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)-quinazolinones are also reported.
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