title: Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides.
abstract: Depending on the reaction conditions,N,N',N''-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetricalN,N',N''-tris(N-acyl-N-benzylamido)guanidines6or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles10were obtained by catalytic hydrogenation of anN-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.
authors.affiliation: Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Szabo
authors.affiliation: Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
authors.forename: Julian
authors.initials: J
authors.lastname: Greiner
authors.affiliation: Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Maas
keywords: 1,2,4-triazolium-3-aminides; guanidines; mesoionic compounds; triaminoguanidinium salts