REACTION OF 6-SUBSTITUTED 3-AMINO-2-ARYL-4(3H)-QUINAZOLINONES WITH D-GLUCOSE AND D-GALACTOSE

The reaction of 6-substituted 3-amino-2-aryl-4(3H)-quinazolinones (1-5 ) with D-glucose and D-galactose in boiling methanol in the presence o f acetic acid as a catalyst yielded a mixture of alpha- and beta-anome rs of 6-substituted N-(D-glycopyranosyl)]-amino-4-(3H)-quinazolinones. The N-glycopyranoside derivatives 6-12 were acetylated with acetic an hydride/pyridine to give the corresponding acetates 13-19. Deacetylati on of 13, 14, 18, 19 gave 6-substituted beta-D-glycopyranosyl)]-amino- 4(3H)-quinazolinones (20-23) as sterically hindered exo- and endo-isom ers.