The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO(3), 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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2686317PMC
http://dx.doi.org/10.3762/bjoc.5.8DOI Listing

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