(The) oxidation of tosylhydrazone and hydrazone derivatives with oxone

Abstract

Tosylhydrazones of carbonyl compounds were found to be readily deprotected into the corresponding carbonyl compounds in good yields by treatment with oxone in aqueous organic solvents such as THF, CH$_3$CN, and MeOH, and by treatment with dimethyldioxirane. However, when the reaction of benzophenone hydrazone with oxone was carried out in aqueous methanol, benzhydryl methyl ether, benzophenone, benzophenone azine, benzhydrol were obtained. 2-Pyridylketone hydrazones were oxidatively cyclized into the corresponding 1.2.3-triazolo[1.5-a] pyridines quantitatively within short reaction time.