A convenient synthesis of novel N-glycosides of 3-(aminophenyl)-4(3H)-quinazolinone derivatives

Authors
Abdel-Megeed, MF El-Hiti, GA Abdo, MA Saleh, MA
Citation
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
Citations number
35
Categorie Soggetti
Chemistry
Journal title
REVUE ROUMAINE DE CHIMIE
ISSN journal
00353930 → ACNP
Volume
45
Issue
6
Year of publication
2000
Pages
545 - 553
Database
ISI
SICI code
0035-3930(200006)45:6<545:ACSONN>2.0.ZU;2-D
Abstract
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.