Syntheses ofUnsymmetric (Sulfoxylidene)ureas from <i>N</i>H‑Sulfoximinesand Dioxazolones Assisted by 2,2,2-Trifluoroethanol

Ureas and sulfoximines are relevant as natural products and pharmaceuticals. The fusion of these two frameworks results in (sulfoxylidene)ureas. Herein, we present a convenient method to access such compounds from <i>N</i>H-sulfoximines and dioxazolones. The reactions are assisted by 2,2,2-trifluoroethanol (TFE), yielding the desired products in moderate to good yields under mild reaction conditions. The process, which involves a Curtius rearrangement, is characterized by its simplicity and the absence of any additional activator rendering it appealing for applications in medicinal chemistry.

Publication Details

Journal
Figshare
Published
2025-03-27
DOI
https://doi.org/10.1021/acs.orglett.5c00512.s001
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Syntheses ofUnsymmetric (Sulfoxylidene)ureas from NH‑Sulfoximinesand Dioxazolones Assisted by 2,2,2-Trifluoroethanol

Figshare
Synthesis and Catalytic Reactions
article

Syntheses ofUnsymmetric (Sulfoxylidene)ureas from NH‑Sulfoximinesand Dioxazolones Assisted by 2,2,2-Trifluoroethanol

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Abstract

Ureas and sulfoximines are relevant as natural products and pharmaceuticals. The fusion of these two frameworks results in (sulfoxylidene)ureas. Herein, we present a convenient method to access such compounds from <i>N</i>H-sulfoximines and dioxazolones. The reactions are assisted by 2,2,2-trifluoroethanol (TFE), yielding the desired products in moderate to good yields under mild reaction conditions. The process, which involves a Curtius rearrangement, is characterized by its simplicity and the absence of any additional activator rendering it appealing for applications in medicinal chemistry.

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Synthesis and Catalytic Reactions
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Syntheses ofUnsymmetric (Sulfoxylidene)ureas from <i>N</i>H‑Sulfoximinesand Dioxazolones Assisted by 2,2,2-Trifluoroethanol · Figshare (2025) | TGRS Research Map | TGRS