Reaction of 2,5‐bis(trifluoromethyl)‐1,3,4‐oxadiazole with primary amines. Synthesis of 4‐substituted‐3,5‐bis(trifluoromethyl)‐4H‐1,2,4‐triazoles

Reaction of 3,5‐bis(trifluoromethyl)‐1,3,4‐oxadiazole (1a) with primary amines under a variety of conditions conveniently produced 4‐substituted‐3,5‐bis(trifluoromethyl)‐4H‐1.2,4‐triazoles 4a in 26‐85% yield. Alkyl amines reacted with 1a in methanol at −42° to provide hydrogen‐bonded monoadduct‐methanol complexes 5a, as determined by X‐ray. The reaction of 1a with sterically hindered or strongly electron deficient anilines required high temperatures in the absence of solvent.