Collect. Czech. Chem. Commun. 1995, 60, 1016-1025

Reaction of 6-Substituted 3-Amino-2-phenyl-4(3H)- Quinazolinones with D-Ribose and L-Arabinose

Mohamed F. Abdel-Megeed, Mohamed A. Saleh*, Mohamed A. Abdo and Gamal A. El-Hiti

Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt


Condensation of 3-amino-2-phenyl-4(3H)-quinazolinone (Ia) and 3-amino-6-bromo-2-phenyl-4(3H)-quinazolinone (Ib) with D-ribose and L-arabinose in boiling methanol gave the corresponding N-glycosides IIa, IIIa, IIb and IIIb. Acetylation of compounds II and III, followed by Zemplen's deacetylation, afforded the N-acetyl derivatives VIa, VIb, VIIa and VIIb. According to their NMR spectra in solution, the N-ribosides exist as β-pyranosides in the 4C1 (D) conformation whereas the N-arabinosides are α-pyranosides in the 4C1 (L) conformation.