The synthesis of 3-methyl-6-R-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

Authors

DOI:

https://doi.org/10.24959/ophcj.20.195727

Keywords:

synthesis, 1, 2, 4-triazoles, physicochemical properties

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-4H-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-4H-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. 1H NMR spectra of the compounds synthesized were recorded on a Varian Mercury VX-200 spectrometer operating at a frequency of 200 MHz, in DMSO-d6, 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 1Н NMR spectroscopy, LC-MS and elemental analysis. 

Received: 18.02.2020
Revised: 29.04.2020
Accepted: 29.05.2020

Supporting Agencies

  • The theme of the Ministry of Public Health of Ukraine
  • No. 0120U101649

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Published

2020-06-18

How to Cite

(1)
Hlazunova, T. V.; Panasenko, O. I.; Knysh, Y. G. The Synthesis of 3-Methyl-6-R-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives. J. Org. Pharm. Chem. 2020, 18, 40-43.

Issue

Vol. 18 No. 2(70) (2020)

Section

Original Researches

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