AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD
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Keywords

2-(2-oxo-2-phenylethylthio)-py­ri­midines, amination, sulfonate method.

How to Cite

Yavolovskii, A., Davtian, A., Grishchuk, L., Pluzhnik-Glagyr, S., Rakipov, I., Ivanov, Y., Chikhichin, D., & Kamalov, G. (2023). AMINATION OF 2-(2-OXO-2-ARYLETHYLTHIO)-PYRIMIDIN-4(3H)-ONE DERIVATIVES USING THE SULFONATE METHOD. Ukrainian Chemistry Journal, 89(1), 60-67. https://doi.org/10.33609/2708-129X.89.01.2023.60-67

Abstract

A Derivatives of 2-thiouracil are characteri­zed by wide spectrum of biological activity, which is characteristic of most representatives this heterocycles class. In particular, 2-(2-oxo-2-phenylethylthio)-pyrimi­din-4(3H)-ones belong to the group of non-nucleoside inhibitors of HIV-1 reverse transcriptase. The antimalarial properties of 2-(2-oxo-2-phenylethyl­thio)-4-R-pyrimidine derivatives, which proved to be effective inhibitors of CIpP protease of Plasmodium falciparum, are being studied. Known examples of 2-(2-oxo-2-phenylethyl­thio)-pyrimidines modification at the "4" position of the heterocycle are limited to use 4-chloro derivatives, which, in turn, are formed according to the classical method by reaction of pyrimidine-4(3H)-ones with POCl3 at boiling point of reaction mixture. In this work, we present an alternative version of modification the above-mentioned class of compounds. By amination amide function of 6-R-2-(2-oxo-2-arylethylthio)-pyrimidin-4(3H)-ones derivati­ves of with ethanolamine and 1-aminopropa­ne-2,3-diol using sulfonate method, synthesized and characterized new compounds a 6-R-2-(2-oxo-2-phenylethylthio)-pyrimidines series by spectral methods. The advantages of this scheme are discussed (the formation of intermediate sulfonates and the amination stage do not require harsh conditions and are carried out with satisfactory yields). The proposed scheme can be recommended in cases where the original substrate contains functio­nal groups that are labile at high temperatures and sensitive to an acidic environment.

https://doi.org/10.33609/2708-129X.89.01.2023.60-67
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References

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