Synthesis and antimicrobial activity of some new heterocycles incorporating the pyrazolopyridine moiety

Abstract

2-Cyano-N-(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)acetamide (2) was utilized as key intermediate for the synthesis of some new coumarin 3, pyridine 4, pyrrole 5, thiazole 8, pyrido[2',3':3,4]-pyrazolo-[5,1-c]triazine 7, and aminopyrazolo 10 compounds. 2-Cyano-N-(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-(dimethylamino)acrylamide (11) was synthesized and allowed to react with hydroxylamine, hydrazine, and guanidine to afford regioselectively the isoxazole 13, pyrazole 15, and pyrimidine 17 derivatives, respectively. The reaction of 11 with thiourea and/or with ethyl glycinate in basic medium afforded the regioisomeric pyrimidinethione 18 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 23. All the synthesized products were tested and evaluated as antimicrobial agents.

Keywords: Aminopyrazole; Antimicrobial activity; Pyrazolo[3,4-b]pyridine; Pyridine; Pyrimidine.