REACTION OF 6-SUBSTITUTED 3-AMINO-2-PHENYL-4(3H)QUINAZOLINONES WITH D-RIBOSE AND L-ARABINOSE

Authors
ABDELMEGEED MF SALEH MA ABDO MA ELHITI GA
Citation
Mf. Abdelmegeed et al., REACTION OF 6-SUBSTITUTED 3-AMINO-2-PHENYL-4(3H)QUINAZOLINONES WITH D-RIBOSE AND L-ARABINOSE, Collection of Czechoslovak Chemical Communications, 60(6), 1995, pp. 1016-1025
Citations number
8
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
60
Issue
6
Year of publication
1995
Pages
1016 - 1025
Database
ISI
SICI code
0010-0765(1995)60:6<1016:RO63WD>2.0.ZU;2-C
Abstract
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 methonol gave the corresponding N-glycosides IIa, IIIa, II b and IIIb. Acetylation of compounds II and III, followed by Zemplen's deacetylation, afforded the N-acetyl derivatives VIa, VIb, VIIa and V IIb. According to their NMR spectra in solution, the N-ribosides exist as beta-pyranosides in the C-4(1) (D) conformation whereas the N-arab inosides are alpha-pyranosides in the C-4(1) (L) conformation.