Synthesis and crystal structure analysis of 2-(4-methyl-2′-biphenyl)-4-amino-1,2,4-triazole-3-thiol

Abstract

The bioactive compound 2-(4-methyl-2 -biphenyl)-4-amino-1,2,4-triazole-3-thiol, F.W. 282.09 was synthesized, characterized by spectroscopic techniques and confirmed by X-ray crystal structure analysis. The title compound crystallizes in monoclinic class under the space group P2 1 /c with cell parameters, a = 11.273(3) Å, b = 17.245(1) Å, c = 7.413(1) Å, β = 97.742(5) • and Z = 4. The structure exhibits inter-molecular hydrogen bonding of the type N-H···S.

Experimental and theoretical structural studies on 4-(2-phenylethyl)-5-(2-furyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

“…The location of the H-atom on N3 rather than S1 and the lengths of the N3-C6 [1.339(6) Å ] and C6-S1 [1.677 (7) Å ] bonds indicate that the molecule exists as the thione form (1a) in the solid state. These values are comparable to those in some related compounds which contain the thionesubstituted 1, 2, 4-triazole group [11,[20][21][22][23][24][25].…”

“…2). The same types of inter-molecular interactions are reported in the articles including amino-and thionesubstituted compounds in [11,21,24,25]. In the molecule, there is one intra-molecular hydrogen bond between the ethyl group and the furan O atom.…”

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

“…It has been well investigated that alkyl hydrazides as an important class of effective building blocks for the preparation of nitrogenous heterocycles, especially for the synthesis of 1,2,4-triazole derivatives have caused much interest and a lot of works have been directed towards their developments [97][98][99][100][101]. Cyclization of formhydrazide with 2,3-dihydro-1H-indene thioamide 66, a product of amide with Lawesson's reagent in toluene, successfully provided triazole intermediate 67 in yield of 22% under the catalysis of mercury acetate (Scheme 25), In comparison with the relatively low yield of this compound, the final target triazole compound as the potent sodium glucose co-transporter 2 (SGLT2) inhibitor unexpectedly exhibited a highly antidiabetic activity.…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 17, 2006) and the discipline

“…As a part of continued efforts toward incorporation of the active 1,2,4-triazole nucleus to the biphenyl ring for the purpose of the synthesis and study of the biological properties of condensed nitrogen and sulfur-containing heterocycles [56][57][58] Swamy et al [59] studied the synthesis and characterization of the bioactive compound 2-(4-methyl-2 0 -biphenyl)-4-amino-1,2,4-triazole-3-thiol using spectroscopic techniques and X-ray crystal structure analysis. The compound crystallizes in monoclinic class under the space group P2 1 /c and exhibits inter-molecular hydrogen bonding of the type N-HÁÁÁS.…”