T. V. Hlazunova, O. Panasenko, Ye. G. Knysh
Jun 18, 2020
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Journal
Journal of Organic and Pharmaceutical Chemistry
Abstract
Aim. To conduct the synthesis and confirm the structure of 3-methyl-6-R-[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazole derivatives as potential biologically active compounds. Results and discussion . It has been shown that the heterocyclization reaction of 4-amino-5-methyl-4 H -1,2,4-triazole-3-thiol with carboxylic acids in the excess of phosphorus oxychloride yields 3-methyl-6-R-[1,2,4]-triazolo[3,4- b ][1,3,4]thiadiazoles. Experimental part. The reaction of 4-amino-5-methyl-4 H -1,2,4-triazole-3-thiol with the corresponding carboxylic acids was carried out in the excess of phosphorus oxychloride. The mixture was heated for 5 h with subsequent cooling and neutralization to pH 7 using ammonia solution. 1 H NMR spectra of the compounds synthesized were recorded on a Varian Mercury VX-200 spectrometer operating at a frequency of 200 MHz, in DMSO-d 6 , using tetramethylsilane (TMS) as an internal standard. Melting points were measured using a MPA100 device. The elemental analysis was performed on a Elementar Vario EL Cube elemental analyzer. Agilent 1260 Infinity HPLC System equipped with Agilent 6120 mass spectrometer were used for registering LC-MS data. Conclusions. As a result of this study 10 new compounds of the 3-methyl-6-R-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole series have been obtained. The structure and purity of the products have been confirmed using 1 Н NMR spectroscopy, LC-MS and elemental analysis. Received : 18.02.2020 Revised : 29.04.2020 Accepted : 29.05.2020