Reactivity of 2-Ethoxyquinazolin- 4-yl hydrazine and its Use in Synthesis of Novel Quinazoline Derivatives of Antimicrobial Activity

Abstract

[Abstract]   The reactions of 2-ethoxy-4-hydrazinoquinazoline 2 withdiethyl oxalate and ethyl chloroacetategave 6-ethoxy-2H-[1,2,4]triazino[4,3-c]quinazoline-3,4-dione 3 and 6-ethoxy-2,3-dihydro-4H-[1,2,4]triazino[4,3-c]quinazolin-4-one 4 respectively.  A series of 5-ethoxy-2-X-[1,2,4]triazolo[1, 5-c]quinazolines  5a-d  was also produced  by reacting2 with theacid chlorides namely: benzoyl,crotonyl,cinnamyland2-furoyl chloridesvia Dimroth rearrangement. Also,2 reacted withethylchloroformate giving   6. Condensation of2withacetone gaveSchiff  base7,and with monosaccharides  gave the  sugarhydrazones 8a-e which were thereafter acetylated  giving the corresponding 9a-e.  Cyclization  of  8a-e byiron(III)chloridegavetriazoloquinazolines10a-e acyclic  C-nucleosides which, by acetylation, afforded  11a-e.  All productswereconfirmed by elemental,  IR, MS, and ¹H-NMR analysis.   Products 8-11 were chosen for biological screening test against gram(+ ive) and gram(- ive) bacteria.