Frontiers in Chemistry (Jun 2020)

I2/DMSO-Catalyzed Transformation of N-tosylhydrazones to 1,2,3-thiadiazoles

  • Weiwei Li,
  • Jun Zhang,
  • Jing He,
  • Liang Xu,
  • Luigi Vaccaro,
  • Ping Liu,
  • Yanlong Gu

DOI
https://doi.org/10.3389/fchem.2020.00466
Journal volume & issue
Vol. 8

Abstract

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An iodine/DMSO catalyzed selective cyclization of N-tosylhydrazones with sulfur without adding external oxidant was developed for the synthesis of 4-aryl-1,2,3-thiadiazoles. In this reaction, oxidation of HI by using DMSO as dual oxidant and solvent is the key, which allowed the regeneration of I2, ensuring thus the success of the synthesis. This protocol features by simple operation, high step-economy (one-pot fashion), broad substrate scope as well as scale-up ability.

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