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 derivative...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-12, Vol.86 (24), p.18004-18016
Main Authors: Shukla, Gaurav, Saha, Priya, Pali, Pragya, Raghuvanshi, Keshav, Singh, Maya Shankar
Format: Article
Language:English
Subjects:
Cyclization
Hydrazones
Oxidation-Reduction
Thiadiazoles
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02275