I2-Mediated Synthesis of 1,3,4-Oxa/thiadiazoles from Aroylhydrazide and Acetonitrile/Thioacetamide

J Org Chem. 2024 Nov 1;89(21):15490-15496. doi: 10.1021/acs.joc.4c01513. Epub 2024 Oct 23.

Abstract

A facile and convenient metal-free direct oxidative amination of acetonitrile followed by cyclization with aroyl hydrazide for synthesizing oxadiazoles has been investigated. Disubstituted 1,3,4-oxadiazoles were obtained at 50-82% yields using readily available acetonitrile as both reagent and solvent. In addition, the reaction of aroyl hydrazides with thioacetamide and cyanothioacetamide afforded 5-methyl-2-aryl-1,3,4-thiadiazoles and 2-aryl-1,3,4-oxadiazole-2-acetonitriles as the main products, respectively.