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Molecules 2010, 15(5), 3302-3310; doi:10.3390/molecules15053302
Article

Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines

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Received: 24 December 2009 / Revised: 15 March 2010 / Accepted: 23 April 2010 / Published: 4 May 2010
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Abstract

Arylhydrazonomalononitriles 1a,b react with phenylhydrazine to yield amidrazones 2a,b that cyclize to give 2-aryl-5-phenylhydrazono-2,5-dihydro-[1,2,4]-triazine-6-carbonitriles 5a,b upon reaction with dimethylformamide dimethylacetal (DMFDMA). Refluxing 5a,b in glacial acetic acid resulted in the formation of the pyrazolo-1,2,4-triazines 6a,b. Compounds 6a,b were also formed upon treatment of 3-amino-4-phenylhydrazono-1-phenyl-2-pyrazolin-5-ones 7a,b with DMFDMA. Reacting these triazinyl arylhydrazononitriles 5a,b with hydroxylamine hydrochloride in ethanolic sodium acetate afforded amidrazones 8a,b that are readily cyclized in refluxing dimethylformamide into [1,2,4]triazino[1,2,3]triazines 10a,b.
Keywords: amidrazones; arylhydrazononitrile; amidoximes; [1,2,4]triazino[1,2,3]triazine; dimethylformamide; dimethylacetal; pyrazolo[1,2,4]triazine amidrazones; arylhydrazononitrile; amidoximes; [1,2,4]triazino[1,2,3]triazine; dimethylformamide; dimethylacetal; pyrazolo[1,2,4]triazine
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Al-Matar, H.M.; Khalil, K.D.; Al-Dorri, D.M.; Elnagdi, M.H. Efficient Routes to Pyrazolo[3,4-e][1,2,4]triazines and a New Ring System: [1,2,4]Triazino[5,6-d][1,2,3]triazines. Molecules 2010, 15, 3302-3310.

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