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.docVIP

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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.doc

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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; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules 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 Hamad Mohamed Al-Matar 1,*, Khaled Dessouky Khalil 2, Doa’a Mohamed Al-Dorri 1 and Mohamed Helmy Elnagdi 1 1 Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait; E-Mail: shelmy1941@ (M.H.E.) 2 Chemistry Department, Faculty of Science, Cairo University, Giza 12613, Egypt; E-Mail: khd.khalil@ (K.D.K.) * Author to whom correspondence should be addressed; E-Mail: h.almatar@.kw. Received: 24 December 2009; in revised form: 15 March 2010 / Accepted: 23 April 2010 / Published: 4 May 2010 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 Introduction Arylhydrazonomalononitriles 1 are synthetically useful reagents that have been utilized in the past as precursors to 4-arylazo-3,5-pyrazolediamines as well as [1,2,3]triazoleamines and pyrazolo[1,5- a]pyrimidines [1]. While reaction o