CC BY-NC-ND 4.0 · Synthesis 2023; 55(08): 1221-1226
DOI: 10.1055/s-0042-1751401
paper

An Efficient Catalyst-Free Direct Approach to 5-Polyfluoroalkyl-1,2,4-triazole-3-thiones

Oksana M. Holovko-Kamoshenkova
a   Uzhhorod National University, Faculty of Chemistry, Department of Organic Chemistry, Narodna ploshcha 3, 88000 Uzhhorod, Ukraine
b   Charles University, Faculty of Science, Department of Organic Chemistry, Hlavova 8, 12843 Praha, Czech Republic
,
a   Uzhhorod National University, Faculty of Chemistry, Department of Organic Chemistry, Narodna ploshcha 3, 88000 Uzhhorod, Ukraine
,
Radim Hrdina
b   Charles University, Faculty of Science, Department of Organic Chemistry, Hlavova 8, 12843 Praha, Czech Republic
,
Vyacheslav N. Baumer
c   SSI ‘Institute for Single Crystals’ NASU, 61001 Kharkiv, Ukraine
,
Nataliya I. Korol
a   Uzhhorod National University, Faculty of Chemistry, Department of Organic Chemistry, Narodna ploshcha 3, 88000 Uzhhorod, Ukraine
,
Liubov V. Sokolenko
d   Institute of Organic Chemistry NASU, 01001 Kyiv, Ukraine
,
Vasil G. Lendel
a   Uzhhorod National University, Faculty of Chemistry, Department of Organic Chemistry, Narodna ploshcha 3, 88000 Uzhhorod, Ukraine
› Author Affiliations

This study was partially supported by the Ministry of Education and Science of Ukraine (State Budget Projects 0119U100232 and 0120U100431).


Abstract

An easy to handle high-efficient approach to 5-polyfluoroalkyl-1,2,4-triazole-3-thiones (11 examples, up to 91% yield) is reported. The tautomerism of thione and thiol forms for the obtained products is discussed. A one step procedure for 6,6-dimethyl-3-(trifluoromethyl)-5,6-dihydro[1,3]thiazolo[2,3-c][1,2,4]triazole formation from trifluoroacetic acid and 4-methallylthiosemicarbazide has been developed. The structures of the products were unambiguously determined by complex NMR investigation and by single crystal X-ray diffraction.

Supporting Information



Publication History

Received: 02 January 2022

Accepted after revision: 28 November 2022

Article published online:
05 January 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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