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Synthesis of Glycosides Containing Quinazolin-4(3H)-one Ring System

2005; Elsevier BV; Volume: 65; Issue: 12 Linguagem: Inglês

10.3987/rev-05-602

1881-0942

Gamal A. El‐Hiti, Mohamed F. Abdel‐Megeed,

Synthesis and biological activity

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 αand 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.CONTENTS 1. 4.4.S-Glycopyranosides of 3-phenylamino-2-thioquinazolin-4(3H)-one 5. CONCLUSION 6. REFERENCES 1.