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http://dx.doi.org/10.5012/jkcs.2013.57.5.612

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  

Khalil, Mohamed A. (Chemistry Department, Faculty of Science, Aswan University)
Sayed, Samia M. (Chemistry Department, Faculty of Science, Aswan University)
Raslan, Mohamed A. (Chemistry Department, Faculty of Science, Aswan University)
Publication Information
Journal of the Korean Chemical Society / v.57, no.5, 2013 , pp. 612-617 More about this Journal
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-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.
Keywords
3-Oxopropanenitrile; Pyrazolo[5,1-c]triazine; Triazolo[5,1-c]triazine; Triazino[4,3-b]indazole; Benzimidazo[2,1-c]triazine;
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