Divergent Thioamide Synthesis via <i>Umpolung</i> C–N Bond Formation from Nitroethane in Aqueous Medium

We present a diverse synthesis of thioamides by installing elemental sulfur and amines in nitroethane <i>via</i> umpolung C-N bond formation. The uniqueness of this water-based protocol renders it more convenient for thioamide synthesis at room temperature. These mild reaction conditions ensure wide functional group tolerance, facilitating late-stage functionalization of drug scaffolds, including intermediates relevant to active pharmaceutical ingredient (API) synthesis.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-03-27
DOI
https://doi.org/10.1021/acs.joc.5c02880
Primary Topic
Synthesis and Reactivity of Sulfur-Containing Compounds
Type
article
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article

Divergent Thioamide Synthesis via Umpolung C–N Bond Formation from Nitroethane in Aqueous Medium

Priyamvada Singh, Brijesh Rathi, Padam Raj Bhatt, Ankush Gupta et al.
The Journal of Organic Chemistry
Synthesis and Reactivity of Sulfur-Containing Compounds
article

Divergent Thioamide Synthesis via Umpolung C–N Bond Formation from Nitroethane in Aqueous Medium

Priyamvada Singh, Brijesh Rathi, Padam Raj Bhatt, Ankush Gupta, Himanshi Sharma
article en

Abstract

We present a diverse synthesis of thioamides by installing elemental sulfur and amines in nitroethane <i>via</i> umpolung C-N bond formation. The uniqueness of this water-based protocol renders it more convenient for thioamide synthesis at room temperature. These mild reaction conditions ensure wide functional group tolerance, facilitating late-stage functionalization of drug scaffolds, including intermediates relevant to active pharmaceutical ingredient (API) synthesis.

The Journal of Organic Chemistry
University of Delhi (IN), Hanover College (US)
Clean water and sanitation
Openalex Percentile: Top 6%
Synthesis and Reactivity of Sulfur-Containing Compounds
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