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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. 2010

Hamad Mohamed Al-Matar, and Khaled Dessouky Khalil, and Doa'a Mohamed Al-Dorri, and Mohamed Helmy Elnagdi
Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait. h.almatar@ku.edu.kw

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.

UI MeSH Term Description Entries
D009570 Nitriles Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE. Nitrile
D010659 Phenylhydrazines Diazo derivatives of aniline, used as a reagent for sugars, ketones, and aldehydes. (Dorland, 28th ed)
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines
D047069 Pyrazolones Compounds with a five-membered heterocyclic ring with two nitrogens and a keto OXYGEN. Some are inhibitors of TNF-ALPHA production. Pyrazolin-5-Ones,Pyrazolin 5 Ones

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