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Syntheses Of 3-(substituted)-2,4,6-triphenylverdazyls

Alan R. Katritzky, Sergei A. Belyakov, H. Dupont Durst, Ruixin Xu, Naresh S. Dalal

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Two series of 2,4,6-triphenylverdazyls substituted at the C(3) position of the heterocyclic ring are obtained using new convenient synthetic methodology. Thus, crown ether assisted solid–liquid phase-transfer catalysis promotes the formation of 3-n-alkyl-substituted 2,4,6-triphenylverdazyls in the reactions of 1,3,5-triphenylformazan with n-alkyl bromides. Under PTC conditions, methylation of 3-(4-nitrophenyl)-1,5-diphenylformazan with methyl iodide exclusively gives the corresponding verdazyl radical. 3-Substituted 2,4,6-triphenylverdazyls containing various di(cyclo)alkylamino moieties at the C(3) position of the verdazyl ring are prepared by the reaction of 1,3,5-triphenylformazan with the corresponding 1-[N,N-di(cyclo)alkylaminomethyl]benzotriazoles under the efficient catalysis of barium hydroxide monohydrate. Sonication of this reaction allows the yields of the verdazyls to be substantially increased. A bis-verdazyl N,N-bonded in the C(3) positions was synthesized. All the radicals obtained were characterized by microanalysis, and by UV–visible and ESR spectroscopy.