Abstract
The synthesis of new biologically active compounds that will replace expensive foreign medicines at the pharmaceutical market of Ukraine is one of the most important directions in development of modern pharmacy and medicine. The synthesis, study of physicochemical and biological properties of new compounds containing 1,2,4-triazole and 1 H -tetrazole cores are important tasks of modern synthetic chemistry. Aim. To synthesize new highly efficient and low-toxic substances, namely alkil-2-((5-(1 Н -tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates, and study physicochemical properties of all compounds synthesized. Results and discussion. Twelve new compounds have been obtained as a result of synthetic transformations, the structure of compounds synthesized has been confirmed by modern complex of physicochemical methods of analysis (IR-spectrophotometry, 1 H NMR-spectroscopy, elemental analysis), and their individuality has been proven on an Agilent 1260 Infinity HPLC high-performance liquid chromatograph equipped with an Agilent 6120 mass spectrometer. Experimental part. As starting materials for the synthesis of alkil-2-((5-(1 Н -tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates the corresponding 2-((5-(1 Н -tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)aceto(propane,benzo)nitriles were used. The synthesis was carried out in the absolute alcohol medium (propanol, butanol, octanol or allyl alcohol) with chloroform. Conclusions. During synthetic and physicochemical studies the preparative methods for the synthesis of alkil-2-((5-(1 Н -tetrazole-1-yl)methyl-4-R-1,2,4-triazole-3-yl)thio)etan(propan,benz)imidates have been developed, the structure of the compounds synthesized has been determined and finally confirmed.
Highlights
Twelve new compounds have been obtained as a result of synthetic transformations, the structure of compounds synthesized has been confirmed by modern complex of physicochemical methods of analysis (IR-spectrophotometry, 1H NMR-spectroscopy, elemental analysis), and their individuality has been proven on an Agilent 1260 Infinity HPLC high-performance liquid chromatograph equipped with an Agilent 6120 mass spectrometer
The mixture was cooled to the temperature of -5 °C and saturated with the flow of dry hydrogen chloride till the weight increment of 2 Mole in relation to 2-(3-thio-5-(1Н-tetrazole-1-yl)methyl-4R-4Н-1,2,4-triazole-3-yl)aceto(propano,benzo)nitriles [1,2,3,4,5,6]
The highest yields were fixed for propyl-2-(3-thio5-(1Н-tetrazole-1-yl)methyl-4-phenyl-4Н-1,2,4-triazole-3-yl) propanimidate (77 %) and propyl-2-(3-thio5-(1Н-tetrazole-1-yl)methyl-4-phenyl-4Н-1,2,4-triazole-3-yl)acetimidate (80 %)
Summary
For the purpose of our work, namely to obtain alkyl-2-(3-thio-5-(1Н-tetrazole-1-yl)methyl-4-R-4Н1,2,4-triazole-3-yl)ethan(propan,benz)imidates as the initial substances for further research 2-(3-thio5-(1Н-tetrazole-1-yl)methyl-4-R-4Н-1,2,4-triazole3-yl)aceto(propano,benzo) nitrile (compounds [1,2,3,4,5,6], Fig. 1) were used. Alkyl-2-(3-thio-5-(1Н-tetrazole-1-yl)methyl4-R-4Н-1,2,4-triazole-3-yl)ethan(propan,benz)imidates [7-18] was obtained with the yields of 42-80 %. Physical and chemical characteristics of alkyl-2-(3-thio-5-(1Н-tetrazole-1-yl)methyl-4-R-4Н-1,2,4-triazole-3-yl) ethan(propan,benz)imidates. Results of elemental analysis of alkyl-2-(3-thio-5-(1Н-tetrazole-1-yl)methyl-4-R-4Н-1,2,4-triazole-3-yl) ethan(propan,benz)imidates. 1,2,4-triazole-3-yl)ethan(propan,benz) imidates are characterized by the intensive singlets fixed in the range of 9.45-10.15 mp and 4.58-5.34 mp, which are the evidence of the presence of protons of tetrazolemethylene groups in the structure of all compounds.
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