Metal-Free Synthesis Of 1,3,4-Oxadiazoles From N '-(Arylmethyl)Hydrazides Or 1-(Arylmethyl)-2-(Arylmethylene)Hydrazines

An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.