Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines

Abstract

Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from their IR, Mass, ¹H NMR, and ¹³C NMR spectra. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazoles from cyclopentanone, primary amines, N-isocyaniminotriphenylphosphorane and aromatic carboxylic acids. Easy work-up, high yields and fairly mild reaction conditions make it a useful procedure in comparison to the modern synthetic methodologies.