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

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• 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. Keywords: guanidines; mesoionic compounds; triaminoguanidinium salts; 1,2,4-triazolium-3-aminides; Introduction Easily accessible by

• , triaminoguanidinium salts or the neutral triaminoguanidine have been reacted with carbonyl compounds. Reactions with aldehydes [3][4][5][6][7] or ketones [8][9][10] yielded the corresponding tris(iminyl)guanidines; cyclocondensation of pentane-2,4-dione at one hydrazinyl branch of TAG-Cl afforded a pyrazole which

Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates

• Jan Szabo,
• Kerstin Karger,
• Nicolas Bucher and
• Gerhard Maas

Beilstein J. Org. Chem. 2014, 10, 2255–2262, doi:10.3762/bjoc.10.234

• triaminoguanidinium salts underwent a threefold carbamoylation with aryl isocyanates to furnish 1,2,3-tris(ureido)guanidinium salts, while p-toluenesulfonyl isocyanate led only to a mono-ureido guanidinium salt. With aryl isothiocyanates, 3-hydrazino-1H-1,2,4-triazole-5(4H)-thione derivatives were obtained. Compounds

• (arylideneamino)- and tris(alkylideneamino)guanidinium salts [7][8][9]; these were the first examples of a threefold symmetrical functionalization of the triaminoguanidinium ion. On the other hand, reactions of triaminoguanidinium salts with carboxylic acids generated 4-amino-3-hydrazinyl-1,2,4-triazoles [10][11

• 1,2,3-triazidoguanidinium salt [16][17]. Direct N-alkylation reactions of the triaminoguanidinium ion are not known. Triaminoguanidinium salts are soluble only in water or in hot alcohol/water mixtures, but not in the common organic solvents, which prevents the use of alkylating reagents such as alkyl