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Review | Regular issue | Vol 65, No. 12, 2005, pp.3007-3041
Published online, 22nd September, 2005
DOI: 10.3987/REV-05-602
Synthesis of Glycosides Containing Quinazolin-4(3H)-one Ring System

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

*Centre for Clean Chemistry, Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea SA2 8PP, U.K.

Abstract

Reactions of various aminoquinazolin-4(3H)-ones with monosaccharides in the presence of a catalytic amount of glacial acetic acid afforded the corresponding N-glycosylamines as a mixture of α- and β-anomers. Acetylation of this mixture gave the corresponding β-glycoside acetates. However, β-glycoside acetates could be obtained directly from reactions of per-O-acetyl-α-D-glucosyl bromides with quinazolin-4(3H)-one derivatives which deacetyalted to the corresponding β-glycosides. A series of S-glycosides have been synthesised from reaction of per-O-acetyl-α-D-glucosyl bromides with quinazolinethiones.