The action of amines on 1,3,4-oxadiazolium salts

1,3,4-Oxadiazolium salts react with a wide variety of primary amines and ammonia to yield s-triazolium salts and s-triazoles, respectively; s-triazolo[1,5-a]pyridinium salts and s-triazolo[1,5-a]pyridines are formed from 1,3,4-oxadiazolo[3,2-a]pyridinium perchlorates. Intermediate oxadiazolines or amidrazones resulting from attack of the amine at C-2 of the oxadiazolium ring have been isolated from the reactions of triphenyloxadiazolium perchlorate with aniline, butylamine, secondary amines, and hydrazines. The subsequent fate of these intermediates depends on the nature of the amine and the conditions used.