%0 Journal Article %T 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 %A Shuki Araki %A Satoshi Hirose %A Yoshikazu Konishi %A Masatoshi Nogura %J Beilstein Journal of Organic Chemistry %D 2009 %I %R 10.3762/bjoc.5.8 %X 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. %K formazan %K mesoionic compounds %K nucleophilic substitution %K tetrazolium %K 1 %K 2 %K 4-triazole %U http://dx.doi.org/10.3762/bjoc.5.8