Electrochemical Synthesis of 1,2,3-Thiadiazoles from α-Phenylhydrazones.

We have developed an electrochemical approach for the synthesis of fully substituted 1,2,3-thiadiazoles from α-phenylhydrazones at room temperature, which is very challenging and complementary to the conventional thermal reactions. The key step involves anodic oxidation of phenylhydrazone derivatives at a constant current followed by N,S-heterocyclization. The protocol is remarkable in that it is free of a base and free of an external oxidant and can be converted to a gram scale for postsynthetic drug development with functional thiadiazoles. Most importantly, the electrochemical transformation reflected efficient electro-oxidation with an operationally friendly easy procedure with ample functional molecules. Cyclic voltammograms support the mechanism of this electro-oxidative cyclization process.

Citation

Gaurav Shukla, Priya Saha, Pragya Pali, Keshav Raghuvanshi, Maya Shankar Singh. Electrochemical Synthesis of 1,2,3-Thiadiazoles from α-Phenylhydrazones. The Journal of organic chemistry. 2021 Dec 17;86(24):18004-18016

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PMID: 34818010

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