Divergent Synthesis of Quinoxalines and α-Ketothioamides Enabled by Sequential S–S and C–S Bond Cleavage of Bunte Salts

We introduce a divergent and straightforward synthetic approach for the synthesis of quinoxaline and α-ketothioamide derivatives from easily accessible Bunte salts under mild reaction conditions. The transformation proceeds through an unusual and sequential C–S bond cleavage followed by subsequent S–S bond scission. I 2 -mediated conditions enable the synthesis of quinoxalines with 1,2-diamines, while elemental sulfur promotes the synthesis of α-ketothioamides using primary and secondary amines. The protocol proceeds at room temperature under mild conditions, delivers products in good to excellent yields, and demonstrates broad functional group compatibility and scalability.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-06-17
DOI
https://doi.org/10.1021/acs.joc.6c00529
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

Divergent Synthesis of Quinoxalines and α-Ketothioamides Enabled by Sequential S–S and C–S Bond Cleavage of Bunte Salts

Ashish Kumar Tewari, Suman Gill
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Divergent Synthesis of Quinoxalines and α-Ketothioamides Enabled by Sequential S–S and C–S Bond Cleavage of Bunte Salts

Ashish Kumar Tewari, Suman Gill
article en

Abstract

We introduce a divergent and straightforward synthetic approach for the synthesis of quinoxaline and α-ketothioamide derivatives from easily accessible Bunte salts under mild reaction conditions. The transformation proceeds through an unusual and sequential C–S bond cleavage followed by subsequent S–S bond scission. I 2 -mediated conditions enable the synthesis of quinoxalines with 1,2-diamines, while elemental sulfur promotes the synthesis of α-ketothioamides using primary and secondary amines. The protocol proceeds at room temperature under mild conditions, delivers products in good to excellent yields, and demonstrates broad functional group compatibility and scalability.

The Journal of Organic Chemistry
Shanghai Institute for Science of Science (CN), Banaras Hindu University (IN)
Council of Scientific and Industrial Research, India, University Grants Commission, Banaras Hindu University
Openalex Percentile: Top 13%
Sulfur-Based Synthesis Techniques
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