1,2,3-Triazol-1-imines. 1. The Synthesis and Lead Tetraacetate Oxidation of Biacetyl Benzoylhydrazone Arylhydrazones to the Novel 2-Aryl-N-benzoyl-4,5-dimethyl-1,2,3-triazol-1-imines

Article abstract of DOI:10.1021/jo00034a013

The synthesis and the Pb(OAc)4 oxidation of the mixed bishydrazones of biacetyl 7 was studied.The formation of the novel N-benzoyl-1,2,3-triazol-1-imines 9 from the oxidation of 7 provided support to the proposed in the past mechanism for the oxidation of bis-aroylhydrazones of α-dicarbonyl compounds 4.Thermolysis and photolysis of 9a in DMSO was carried out.The results suggested that benzoylnitrene was formed in the photochemical reaction, and therefore compounds such as 9 could serve as non-azide aroyl nitrene precursors.For 9a the results of the X-ray analysis were correlated with charge densities and bond orders gleaned by the MNDO method.Product 9d was alternatively synthesized by the addition of photochemically generated bezoylnitrene to the 1,2,3-triazole 21.