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Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides

DOI: 10.3762/bjoc.5.8

Keywords: formazan , mesoionic compounds , nucleophilic substitution , tetrazolium , 1 , 2 , 4-triazole

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The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO3, primary and secondary amines undergo a nucleophilic substitution to give the corresponding 5-aminotetrazolium salts. When triethylamine is used as a base, primary amines give 3-phenylazo-1,2,4-triazoles. A plausible dual-path mechanism is proposed for the formation of the triazoles via Type B mesoionic tetrazolium-5-aminides.


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