Mf. Abdel-megeed et al., A convenient synthesis of novel N-glycosides of 3-(aminophenyl)-4(3H)-quinazolinone derivatives, REV RO CHIM, 45(6), 2000, pp. 545-553
Reactions of monosaccharides with 3-(4-aminophenyl) 6-bromo-2-methyl-4(3H)-
quinazolinone (6) and 3-(2-aminophenyl)-6,8-dibromo-2-methyl-4(3H)-quinazol
inone (7) gave stereoselectively beta -N-glycosides 8 and 9, respectively i
n good yields. Acetylation of 8 and 9 gave the corresponding acetyl derivat
ives 10 and 11 in very good yields. However 10b and 11b could be directly o
btained from reaction of 6 and 7 with alpha -acetobromoglucose. Deacetylati
on of 10b and 11b using sodium methoxide followed by ion-exchange resin tre
atment afforded 8b and 9b in a crystalline form.