Abstract
The large synthetic potential and high biological potential in the series of 1,2,4-triazole derivatives cause favorable conditions for the search for new biologically active substances. A special attention is paid to the possibility of introducing various substituents at the stage of 1,2,4-triazole-3-thiol structure formation. At the same time, derivatives of xanthine are known as the basis for obtaining a wide range of drugs. The aim of this work was the synthesis and properties’ study of new compounds in the series of esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acids. Materials and methods. The strategy of the synthesis of all target products of the reaction was based on the use of theophylline as starting material. To obtain the intermediate thiol we used reactions of esterification, nucleophilic substitution, hydrazinolysis and intermolecular alkaline heterocyclic. The esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid were obtained by two methods. The melting point was determined using capillary method on OptiMelt MPA 100 (SRS, USA). The structure of the compounds was confirmed with elemental analysis on Elemental Vario EL cube (Elementar Analysensysteme, Germany), IR spectra (4000–400 cm-1) were taken off the module ALPHA-T of Bruker ALPHA FT-IR spectrometer (Bruker optics, Germany). Chromate-mass-spectral studies were carried out on Agilent 1260 Series LC/MSD System. Conclusion. The optimal conditions of obtaining esters of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid have been determined. 15 not described previously compounds have been synthesized, its structure has been confirmed by physical and chemical methods of analysis. It has been established that the synthesis of esters of 2-[5-((theophylline-7'-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid proceeds with greater yield, if they are gotten directly from the thiol.
Highlights
The aim of this work was the synthesis and properties’ study of new compounds in the series of esters of 2-[5-((theophylline-7ʹ-yl) methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acids
Ethers of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid are widely used in organic chemi cals and pharmaceutical intermediates [2,3,7,8,9,10,11]
Ethers of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3ylthio]acetic acids is an understudied group of compounds, which creates conditions for their own data supplement information regarding this class of compounds
Summary
To achieve this goal the following experimental methods of organic chemistry have been used: synthesis and chemical analysis with using IR-, 1H NMR-spectroscopy, and chromatography-mass-spectrometry and elemental analysis. The esters of 2-[5-((theo phylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid were obtained by two methods. The second method (В) involves esterification 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole3-ylthio]acetic acid with methanol, ethanol, propanol-1, propanol-2 and butanol-1 in the presence of a catalytic amount of concentrated sulfuric acid. Synthesis of 2-[5-((theophylline-7ʹ-yl)methyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid was carried out by known method in double excess of sodium hydroxide with 2-chroacetic acid [6]. The purity and structure of the obtained compounds has been confirmed using 1H NMR spectroscopy, elemental analysis, IR spectrophotometry and gas chromatography-mass spectrometry. A. A mixture of 0.01 mole 2-[5-((theophylline-7ʹ-yl)me thyl)-4-R-1,2,4-triazole-3-ylthio]acetic acid, 35 ml of the appropriate alcohol (methanol, ethanol, propanol-1, propanol-2 and butanol-1) and 1 ml of concentrated sulfuric acid is boiled for 10 hours, the solvent is evaporated, the residue is neutra lized with a solution of sodium hydrogencarbonate. Sample mixing substances obtained by methods A and B gave no depression of melting point
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