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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

1,* , 2
, 1 and 1
1 Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait 2 Chemistry Department, Faculty of Science, Cairo University, Giza 12613, Egypt
* Author to whom correspondence should be addressed.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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