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Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Yuhan Lu, Yadong Sun*, Ablimit Abdukader*, Chenjiang Liu

* School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, P. R. of China, Email: syd19791016163.com, ablimit1970126.com

Y. Lu, Y. Sun, A. Abdukader, C. Liu, Synlett, 2021, 32, 1044-1048.

DOI: 10.1055/a-1473-7369



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Abstract

A highly efficient reaction of readily available tosylhydrazones with ammonium thiocyanate in ecofriendly EtOH as the solvent provides 1,2,3-thiadiazoles in very good yields at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance.

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Key Words

1,2,3-thiadiazoles, transition-metal-free, tosylhydrazones, ammonium thiocyanate, potassium peroxydisulfate, ecofriendly solvents


ID: J72-Y2021