SYNTHESIS OF SOME DERIVATIVES 3-(5-MERCAPTO-[1,3,4]OXADIAZOL-2-YLMETHYL)-5,7-DIMETHYL-3H-THIAZOLO[4,5-B]PYRIDIN-2-ONE AS POTENTIAL BIOLOGICALLY ACTIVE COMPOUNDS
DOI:
https://doi.org/10.11603/2312-0967.2019.1.9930Keywords:
thiazolo[4,5-b]pyridines, cyanethylation, alkylationAbstract
The aim of the work. Expanding the synthetic potential of thiazolo[4,5-b]pyridines, the study of reactivity and synthesis of novel 3-(5-mercapto-[1,3,4]oxadiazol-2-ylmethyl)-5,7-dimethyl-3H-thiazolo[4,5-b]pyridin-2-ones.
Materials and Methods. Methods of organic synthesis, NMR spectroscopy, elemental analysis.
Results and Discussion. To expand the combinatorial library of thiazolopyridines the carried out a structural modification of the thiol group of the 3-(5-mercapto-[1,3,4]oxadiazol-2-ylmethyl)-5,7-dimethyl-3H-thiazolo[4,5-b]pyridin-2-one in reactions cyanoethylation and alkylation. As alkylating agents, monochloroacetate acid ethyl ester and some chloroacetamides were tested, which made it possible to obtain a series of new derivatives of the basic scaffold.
Conclusions. It has been found that 3-(5-mercapto-[1,3,4]oxadiazol-2-ylmethyl)-5,7-dimethyl-3H-thiazolo[4,5-b]pyridin-2-one involved into the reaction cyanoethylation, and also forms salts with alkalis. The obtained salt 3-(5-mercapto-[1,3,4]oxadiazol-2-ylmethyl)-5,7-dimethyl-3H-thiazolo[4,5-b]pyridin-2-one possessing nucleophilic properties and the further involved into alkylation reaction using various alkylating agents like ethylchloroacetate and chloroacetamides. We continue to research different activities and chemical transformation of these substances with the prospect of studying biological activities.
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