STUDIES ON SOM£ QUINAZOLONES AND SOME R.E..LATED COMPOUNDS

Abstract

The present work is a part of a program deals with the study and synthesis of some nitrogen bridge heterocyclic ring systems and their reactivity towards different monosugar moieties and glycosylisothiocyanate in correlation with their spectral and biological activity. N-Glycosides of 3-amino-2,4(1H,3H) quinazolinedione.

3-amino-2,4(1H,3H)quinazolinedione (258) was synthesized by reacting of hydrazine hydrate and 2,4(1H,3H)quinazolinedione (299a) under drastic conditions. Glycosylation was carried out by application of method usually employed for the synthesis ofN-glycosylarylamines. The carbohydrate namely D-glucose, D-xylose and D-arabinose was allowed to react with 3-amino- 2,4(1H,3H)quinazolinedione (258) in boiling methanol in the presence of acetic acid as catalyst. The obtained N-glycosides were submitted to acetylation with acetic anhydrid in pyridine at 0°C and the 0-acetyl derivatives ofN-glycosides 276- 278 were then purified by crystallization.