Synthesis and physical-chemical properties of 6-(5-(1Н-tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-ylthio)pyridin-3-amines and 6-((5-(1Н-tetrazole-1-yl)methil-4-R-1,2,4-triazole-3-ylthio)pyridin-3-yl)-(alk,ar,heter)ylmethanimines
DOI:
https://doi.org/10.14739/2310-1210.2017.1.91726Keywords:
1, 2, 4-triazole, 1H-tetrazole, synthesis, physical-chemical propertiesAbstract
Over the past decade the number of publications, that contain different aspects of chemistry and use of triazoles and tetrazoles have been doubled and continues to grow. Puplications of recent years show that heterocycles with 1,2,3,4-teterazoles and 1,2,4-triazoles are biologically active compounds with a broad spectrum of action. This fact indicates the interest to these compounds as potential objects of modern pharmaceutical market, namely to those compounds which contain both heterocycles.
Purpose – synthesis and establishment of physical-chemical properties of 6-(5-(1Н-tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-ylthio)pyridin-3-amines and 6-((5-(1Н-tetrazole-1-yl)methil-4-R-1,2,4-triazole-3-ylthio)pyridin-3-yl)-(alk,ar,heter)ylmethanimines.
Materials and methods. The melting point has been determined by capillary method. The elemental composition of compounds has been set with the help of elemental analyzer Elementar Vario L cube (CHNS). 1H NMR spectra of obtained compounds has been set with the help of Varian Mercury VX-200, solvent – DMSO-d6, internal standart – Tetramethylsilane. Chromatography-mass spectrometry studies have been conducted on gas-liquid chromatograph Agilent 1260 Infinity HPLC equipped with a mass spectrometer Agilent 6120.
5-(1H-Tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-thioles were used as starting materials for 6-(5-(1Н-tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-ylthio)pyridin-3-amines. Synthesis of the compounds was carried out in a medium of propyl alcohol in the presence of 5-amino-2-chloropyridine.
6-((5-(1Н-tetrazole-1-yl)methil-4-R-1,2,4-triazole-3-ylthio)pyridin-3-yl)-(alk,ar,heter)ylmethanimines were obtained reacting 6-(5-(1Н-tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-ylthio)pyridin-3-amines with the appropriate aldehydes (acetaldehyde, m-anisaldehyde, 2-hydroxybenzaldehyde, 3-fluorobenzaldehyde, 4-fluorobenzaldehyde, 4-diethylaminobenzaldehyd, hydroxynaphthalene) in the acetic acid medium.
Results. 11 New compounds, which have not been described previously, were obtained during the synthetic studies. The computer prediction was performed using PASS online service, it was found that the synthesized 6-(5-(1Н-tetrazole-1-ylmethyl)-4-R-1,2,4-triazole-3-ylthio)pyridin-3-amines and 6-((5-(1Н-tetrazole-1-yl)methil-4-R-1,2,4-triazole-3-ylthio)pyridin-3-yl)-(alk,ar,heter)ylmethanimines are low-toxic compounds and exhibit a wide range of biological actions, which corresponds to literature data.
Conclusions. The results of our work have confirmed the structure of the synthesized compounds, which indicates the possibility of their further use in biological studies.
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