Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 13, Issue -, Pages 579-588Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.57
Keywords
guanidines; mesoionic compounds; triaminoguanidinium salts; 1,2,4-triazolium-3-aminides
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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.
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