Abstract
The versatile, hitherto unreported 3-(4-(2-phenyldiazenyl)-2-oxo-2H-chromen-3-yl)-3-oxopropanenitrile 3 was prepared by two convenient routes: either by the reaction of ethyl 4-(2-phenyldiazenyl)-2-oxo-2H-chromen-3-carboxylate 2 with acetonitrile in the presence of sodium hydride or by treatment of 4-(2-phenyldiazenyl)-3-(2-bromoacetyl)-2H-chromen-2one 5 with potassium cyanide. Reaction of 3 with heterocyclic diazonium salts 6, 7, 14 and 17 furnished the corresponding hydrazones 8, 9, 15 and 18. The latter hydrazones underwent intramolecular cyclization into the corresponding pyrazolo[5,1-c]- 1,2,4-triazine 10, 1,2,4-triazolo[5,1-c]-1,2,4-triazine 11, 1,2,4-triazino[4,3-b] indazole 16 and imidazo[2,1-c]-1,2,4-triazine 19 derivatives, respectively upon refluxing in pyridine.