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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 57, Number 5
JKCSEZ 57(5)
October 20, 2013 

Synthesis of New Pyrazolo[5,1-c]triazine, Triazolo[5,1-c]triazine, Triazino[4,3-b]indazole and Benzimidazo[2,1-c]triazine Derivatives Incorporating Chromen-2-one Moiety
Mohamed A Khalil, Samia M Sayed, Mohamed A Raslan*
3-Oxopropanenitrile, Pyrazolo[5,1-c]triazine, Triazolo[5,1-c]triazine, Triazino[4,3-b]indazole, Benzimidazo[2,1-c]triazine
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-2- one 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.
612 - 617
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