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 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
4
C
1
(D) conformation whereas the
N
-arabinosides are α-pyranosides in the
4
C
1
(L) conformation.