Rearrangement of 2-(2,5-Dioxopyrrolidin-1-yl)guanidine: An Efficient Synthesis and Structure of 3-(5-Amino-1H-1,2,4-triazol-3-yl)propanoic Acid and Derivatives

One-pot, microwave-assisted synthesis of polymethylene-bridged bis(1H-1,2,4-triazol-5(3)-amines) and their tautomerism

“…These signals together with two sets of signals for the triazole ring carbon atoms in the 13 C NMR spectra served for the assignments of two main forms (A and B) of the triazole ring (three potential tautomers). The assignments were confirmed with the literature data, [6][7][8]10 and the equilibrium constant (KT) and corresponding Gibbs free energy (ΔG300) values were estimated (Table 3).…”

“…This reaction under conventional heating was reported to suffer from a lack of selectivity resulting in the formation of a mixture of products, from which pure ethylene-bis(1H-1,2,4-triazol-5-amine) 12 was isolated in 8-11% yield only. 8 To overcome this problem, we optimized the reaction conditions under microwave irradiation.…”

The structure of protonated 3-pyridyl-substituted 5-amino-1H-1,2,4-triazoles: an experimental and theoretical study

“…12,21-24 The pre dicted relative stabilities of the tautomers containing pro tonated triazole moiety (tautomers D-F, see Table 2) are also in excellent agreement with published data. 12,13, 24 A key question is as to how changes in position of the nitrogen atom in the pyridine moiety influence the direc tionality of protonation of molecules 1-3. The results of thermodynamic analysis based on comparison of the free energies of tautomers A-F (see Table 2) show that proto nation of the bases 1-3 should mainly occur at the pyri dine nitrogen atom because the tautomers 4A 2, 5A 2, and 6A dominate in the equilibrium mixtures.…”

Crystal structure of bis[(5-amino-1H-1,2,4-triazol-3-yl-κN4)acetato-κO]diaquanickel(II) dihydrate

“…In a continuation of our work on the synthesis and reactivity of aminotriazole carboxylic acids (Chernyshev et al, 2006(Chernyshev et al, , 2009(Chernyshev et al, , 2010, we have focused our attention on another chelating ligand, namely 2-(5-amino-1H-1,2,4-triazol-3yl)acetic acid (ATAA, Fig. 1), which can be considered as a homologue of ATCA.…”