Tautomerism of aza cycles: I. Structure of 3(5)-butylsulfanyl-5(3)-methyl(phenyl)-1H-1,2,4-triazole tautomers in crystal. Preference of the 3-RA-5-RD-1H-tautomer of 3(5)-mono-and 3,5-disubstituted 1,2,4-triazoles

Бузыкин, Б. И.; Миронова, Е. В.; Набиуллин, В. Н.; Gubaidullin, А. Т.; Литвинов, И. А.

doi:10.1134/s1070363206090209

Cited by 16 publications

(10 citation statements)

References 68 publications

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“…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).…”

Section: A R T I C L E I N F O Abstractsupporting

confidence: 80%

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

Lim

Tiekink

et al. 2018

Tetrahedron Letters

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A highly selective and efficient method for the synthesis of 3,3'(5,5')-polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) was developed using the reaction of dicarboxylic acids and aminoguanidine in an aqueous medium. This one-pot, microwave-promoted method was proved to be scalable affording the desired products in good yields and purity. The scope of the method was successfully explored by the preparation of a small library of polymethylene-bis(1H-1,2,4triazol-5(3)-amines) with different alkyl chain linkers. The annular prototropic tautomerism in the prepared compounds was studied using NMR spectroscopy and X-ray crystallography.

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Section: A R T I C L E I N F O Abstractsupporting

confidence: 80%

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

Lim

Tiekink

et al. 2018

Tetrahedron Letters

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“…19 Surprisingly, we found that the presence of forms A and B in the crystal was possible even for compounds bearing substituents with considerably different electronic properties. Thus, two compounds, that is, 5-amino-3-phenyl-1,2,4-triazole and 3-amino-5-phenyl-1,2,4-triazole (2a) crystallized together in the same crystal (Fig.…”

Section: R Rmentioning

confidence: 96%

An aqueous medium synthesis and tautomerism study of 3(5)-amino-1,2,4-triazoles

Dolzhenko

Pastorin

Dolzhenko

et al. 2009

Tetrahedron Letters

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a b s t r a c tA catalyst-free highly efficient synthesis of 3(5)-amino-5(3)-(het)aryl-1,2,4-triazoles in aqueous medium was performed using conventional heating and microwave irradiation. The tautomerism in the products was investigated using NMR spectroscopy and X-ray crystallography. The effects of the substitution, temperature, solvents, and concentration on the tautomerism were studied. The triazoles were found to exist in 1H-forms, the 4H-form was not observed either in solid state or in solution. In general, 5-amino-1,2,4-triazoles were electronically preferred in the tautomeric equilibrium, but some exceptions from the established relationship were also identified.

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“…For the synthesis, tautomerism and structures of related 1,2,4triazoles, see: Dolzhenko et al (2009aDolzhenko et al ( ,b,c, 2010; Buzykin et al (2006). For related carbethoxythioureas, see: Dolzhenko et al (2010); Huang et al (2009); Lin et al (2004Lin et al ( , 2007; Su et al (2006); Zhang et al (2003Zhang et al ( , 2007.…”

Section: Related Literaturementioning

confidence: 99%

N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea

et al. 2010

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The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C13H16N5O2S, exists in the 3-aryl-5-thioureido-1H-1,2,4-triazole tautomeric form. The molecular structure is stabilized by intramolecular hydrogen bonding (N—H⋯S=C between the endocyclic N-bound H atom and the thioureido S atom, and N—H⋯O=C within the ethoxycarbonylthiourea unit), both arranged in an S(6) graph-set motif. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 6.59 (10)°. In the crystal structure, the molecules form two types of centrosymmetric dimers connected by intermolecular hydrogen bonds; in the first, the N—NH triazole sides of two molecules are connected [R 2 2(6) graph-set motif] and the second is an N—H⋯S=C interaction between the imide H atoms and the thiocarbonyl S atoms [R 2 2(8) graph-set motif]. Together, they form a network parallel to the (111) plane.

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Tautomerism of aza cycles: I. Structure of 3(5)-butylsulfanyl-5(3)-methyl(phenyl)-1H-1,2,4-triazole tautomers in crystal. Preference of the 3-RA-5-RD-1H-tautomer of 3(5)-mono-and 3,5-disubstituted 1,2,4-triazoles

Cited by 16 publications

References 68 publications

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

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

An aqueous medium synthesis and tautomerism study of 3(5)-amino-1,2,4-triazoles

N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea

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