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image of Oxidative Cyclization of (Het)aryl-α-oxothioamides in Acidic DMSO Media: A Convenient Method for the Synthesis of 1,2,4-Thiadiazoles

Abstract

In the present study, we report a facile and novel method for the synthesis of 1,2,4-thiadiazoles from α-oxothioamides using dimethyl sulfoxide (DMSO) as both solvent and reagent under acidic conditions. The reaction proceeds an oxidative cyclization mechanism, offering a convenient and efficient synthetic route. This protocol is operationally simple, does not require harsh conditions, and delivers the desired thiadiazole derivatives in moderate to excellent yields with satisfactory purity. Importantly, this methodology overcomes several synthetic challenges previously encountered in related transformations. The scope of the reaction was demonstrated through a variety of (het)aryl-substituted α-oxothioamides. All synthesized compounds were characterized and confirmed using standard analytical techniques, including 1H-NMR, 13C-NMR, LC-MS, and FT-IR. This strategy provides a valuable approach for the rapid construction of bioactive 1,2,4-thiadiazole scaffolds.

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2025-10-30
2025-12-10

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Oxidative Cyclization of (Het)aryl-α-oxothioamides in Acidic DMSO Media: A Convenient Method for the Synthesis of 1,2,4-Thiadiazoles
Bentham Science Publishers ; https://doi.org/10.2174/0115701786403527251007095346
/content/journals/loc/10.2174/0115701786403527251007095346
/content/journals/loc/10.2174/0115701786403527251007095346
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  • Article Type:     Research Article
Keywords: acid-catalyzed ; dendrodoine ; α-oxothioamides ; thiobenzamide ; anxiolytic ; acetonitrile ; α-oxodithioesters ; oxidative cyclization ; Thiadiazoles

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