Reactivity of 6-methylchromone-3-carbonitrile towards some nitrogen nucleophilic reagents

Abstract

The chemical reactivity of 6-methylchromone-3-carbonitrile (1) was studied towards a variety of nitrogen nucleophiles. A variety of products was obtained from the reaction of carbonitrile 1 with hydrazine hydrate, S-benzyl dithiocarbazate, isonicotinic acid hydrazide and cyanoacetohydrazide. A diversity of Schiff bases bearing 2-amino-6-methylchromone linked variable heterocyclic systems was efficiently synthesized. Reaction of carbonitrile 1 with guanidine and cyanoguanidine resulted in ring conversion producing chromeno[4,3d]pyrimidines. Reaction of carbonitrile 1 was also studied towards some 1,4-binucleophiles.