Synthesis and alkylation of 5-aryl-1,2-dihydro-3H-1,2,4-triazole-3-thiones
Keywords:1,2,4-triazoles; 5-(2,4- and 3,4-dimethoxyphenyl)-3H-1,2,4-triazole-3-thiones; alkylation reactions
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.
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