Reactions of 3-aryl-5-methyl-1,2,4-oxadiazoles with benzyl alcohol and with benzylamine

Abstract

When heated with benzyl alcohol, 3-aryl-5-methyl-1,2,4-oxadiazoles afford mainly the aryl nitrile, benzyl acetate, and benzaldehyde. A number of other products, including 1,3,5-triazines, have been identified. Benzylamine and 5-methyl-1,2,4-oxadiazoles similarly give aryl nitrile and N-acetylbenzylamine, but the reaction is slower. However, in mixtures of the alcohol and the amine, the amine reacts the faster. Possible reaction mechanisms are discussed. The methyl group of the oxadiazole was shown to exchange its protons with those of benzyl alcohol more readily than the oxadiazole otherwise reacted with benzyl alcohol.