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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 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.

SUBMITTER: Szabo J

PROVIDER: S-EPMC5372706 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Szabo Jan J Greiner Julian J Maas Gerhard G

Beilstein journal of organic chemistry 20170322

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 catalyt ...[more]

PMID: 28405238

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