Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp3 C–H functionalization of azaarenes

Abstract

An efficient iodine-mediated one-pot synthetic protocol for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp³ C–H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs₂CO₃. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions and high yields, making this protocol an attractive strategy towards the synthesis of bioactive molecules and their key building blocks.