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

• Main Authors: Jan Szabo, Julian Greiner, Gerhard Maas
• Format: Article
• Language: English
• Published: Beilstein-Institut 2017-03-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: guanidines; mesoionic compounds; triaminoguanidinium salts; 1,2,4-triazolium-3-aminides
• Online Access: https://doi.org/10.3762/bjoc.13.57

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-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.