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Paper | Regular issue | Vol 96, No. 4, 2018, pp.690-706
Published online, 6th March, 2018
DOI: 10.3987/COM-18-13874
Reactivity of 6-Methylchromone-3-carbonitrile Towards Some Nitrogen Nucleophilic Reagents

Nasser M. El-Gohary, Magdy A. Ibrahim,* and Sara Said

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11711, Egypt

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[4,3-d]pyrimidines. Reaction of carbonitrile 1 was also studied towards some 1,4-binucleophiles.