Reaction of benzonitrile N-(p-nitrophenyl)imide with 5-substituted tetrazoles: a new route to substituted 1,2,4-triazoles via N-hydrazonoyltetrazoles

Abstract

A wide range of phenyl 5-R-substituted (R = aryl, alkyl, amino, halo, H) 1- and 2-hydrazonoyltetrazoles has been synthesized. Substituent effects on the orientation of nitrite imide attack on 5-aryltetrazoles are reported. Thermolysis and fragmentation of the resulting hydrazonoyltetrazoles under different conditions gave high yields of a range of substituted 1,2,4-triazoles including aryl, alkyl, amino and azido derivatives. Interesting substituent effects including steric blocking of triazole formation from 5-aryltetrazoles by di-ortho-substitution of the 5-aryl ring are also noted.