Regioselective PyrazoleSynthesis via Base-Mediated[3+2] Cycloaddition of 2‑Alkynyl-1,3-Dithianes and Sydnones

We present a novel base-mediated [3+2] cycloaddition for the regioselective synthesis of polysubstituted pyrazoles using 2-alkynyl-1,3-dithianes and sydnones. By exploiting the umpolung and nucleophilic properties of 2-alkynyl-1,3-dithianes, this method achieves efficient pyrazole construction under mild conditions with excellent regioselectivity, broad functional group tolerance, and diverse substrate compatibility. Furthermore, the unique reactivity of the dithianyl group enables facile derivatization and synthesis of highly functionalized pyrazoles.

Publication Details

Journal
Figshare
Published
2025-02-27
DOI
https://doi.org/10.1021/acs.joc.5c00101.s001
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

Regioselective PyrazoleSynthesis via Base-Mediated[3+2] Cycloaddition of 2‑Alkynyl-1,3-Dithianes and Sydnones

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N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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Regioselective PyrazoleSynthesis via Base-Mediated[3+2] Cycloaddition of 2‑Alkynyl-1,3-Dithianes and Sydnones

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Abstract

We present a novel base-mediated [3+2] cycloaddition for the regioselective synthesis of polysubstituted pyrazoles using 2-alkynyl-1,3-dithianes and sydnones. By exploiting the umpolung and nucleophilic properties of 2-alkynyl-1,3-dithianes, this method achieves efficient pyrazole construction under mild conditions with excellent regioselectivity, broad functional group tolerance, and diverse substrate compatibility. Furthermore, the unique reactivity of the dithianyl group enables facile derivatization and synthesis of highly functionalized pyrazoles.

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N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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Regioselective PyrazoleSynthesis via Base-Mediated[3+2] Cycloaddition of 2‑Alkynyl-1,3-Dithianes and Sydnones · Figshare (2025) | TGRS Research Map | TGRS