Синтез та алкілування 5-арил-1,2-дигідро-3H-1,2,4-триазол-3-тіонів

Dmytro V. Dovbnya; Andrii G. Kaplaushenko; Alla S. Korzhova

doi:10.24959/ophcj.21.188135

Authors

Dmytro V. Dovbnya Zaporizhzhya State Medical University, Ukraine https://orcid.org/0000-0001-6170-144X
Andrii G. Kaplaushenko Zaporizhzhya State Medical University, Ukraine https://orcid.org/0000-0003-3704-5539
Alla S. Korzhova Zaporizhzhya State Medical University, Ukraine https://orcid.org/0000-0002-2034-9010

DOI:

https://doi.org/10.24959/ophcj.21.188135

Keywords:

1,2,4-triazoles; 5-(2,4- and 3,4-dimethoxyphenyl)-3H-1,2,4-triazole-3-thiones; alkylation reactions

Abstract

5-R-1,2,4-triazole-3-thiones and their derivatives are easy to obtain; they have low toxicity and a broad spectrum of the biological activity. It makes this class of heterocyclic compounds promising for creating potential drugs.

Aim. To develop the preparative methods for the synthesis of 5-aryl-1,2-dihydro-3H-1,2,4-triazole-3-thiones and study their reactivity in the alkylation reaction.

Results and discussion. New 5-aryl-1,2-dihydro-3H-1,2,4-triazole-3-thiones were synthesized. The latter were used for the synthesis of 3-aryl-5-(alkylthio)-4H-1,2,4-triazoles.

Experimental part. Using a series of four successive reactions based on the substituted benzoic acids new 5-aryl-1,2-dihydro-3H-1,2,4-triazole-3-thiones were synthesized. Alkylation of the thiones allowed obtaining a series of S-alkyl derivatives. The structure of the compounds synthesized was confirmed by elemental analysis, IR and ¹H NMR spectroscopy, and their individuality was determined by high-performance liquid chromatography.

Conclusions. The preparative methods have been developed, and new 5-aryl-1,2-dihydro-3H-1,2,4-triazole-3-thiones have been synthesized. Alkylation of the latter made it possible to obtain a series of 3-aryl-5-(alkylthio)-4H-1,2,4-triazoles with an alkylthio fragment of different length.

Supporting Agency

Роботу виконано в межах теми «Дослідження синтетичних, фізико-хімічних та біологічних властивостей похідних 5-арил- та 5-гетерил-1,2,4-тріазол-3-тіонів» (№ держреєстрації: 0113U005084; період досліджень: 2018 – 2023).

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