Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris( acylamino) guanidines and mesoionic 1,2,4-triazolium-3-aminides

Depending on the reaction conditions, N, N', N''-tris(benzylamino) guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N, N', N''-tris(N-acyl-N-benzylamido) guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.