Synthesis of glycosides containing quinazolin-4(3H)-one ring System

El-Hiti, Gamal A. and Abdel-Megeed, Mohamed F. 2005. Synthesis of glycosides containing quinazolin-4(3H)-one ring System. Heterocyles 65 (12) , pp. 3007-3041. 10.3987/REV-05-602

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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 b- and a-anomers. Acetylation of this mixture gave the corresponding b-glycoside acetates. However, b-glycoside acetates could be obtained directly from reactions of per-O-acetyl-b-D-glucosyl bromides with quinazolin-4(3H)-one derivatives which deacetyalted to the corresponding b-glycosides. A series of S-glycosides have been synthesised from reaction of per-O-acetyl-b-D-glucosyl bromides with quinazolinethiones.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Aminoquinazolin-4(3H)-one ; N-Glycopyranosylamine ; Monosaccharide ; Condensation ; Acetylation
Publisher:	Japan Institute of Heterocyclic Chemistry
ISSN:	1881-0942
Last Modified:	19 Mar 2016 22:24
URI:	https://orca.cardiff.ac.uk/id/eprint/15365

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