Copper(I)-Catalyzed Interrupted CuAIAC/Disulfuration Reaction for the Synthesis of <i>N,N</i> ′-Bicyclic Pyrazolidinone Disulfides

A series of <i>N,N</i>'-bicyclic pyrazolidinone disulfides were prepared via a copper(I)-catalyzed interrupted CuAIAC/disulfuration cascade reaction. This protocol proceeded through a copper(I)-catalyzed azomethine imine-alkyne cycloaddition, followed by the interception of the in situ-formed cuprate-pyrazolidinonate intermediate with trisulfide dioxides. The reaction exhibits complete regioselectivity, mild conditions, and broad functional group compatibility, including halogen, cyano, and heterocycle, making it a highly efficient synthetic strategy.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-22
DOI
https://doi.org/10.1021/acs.joc.5c02696
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Copper(I)-Catalyzed Interrupted CuAIAC/Disulfuration Reaction for the Synthesis of N,N ′-Bicyclic Pyrazolidinone Disulfides

Younan Wang, Yuan Wang, Jingyu Wang, Weiguo Wang
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Copper(I)-Catalyzed Interrupted CuAIAC/Disulfuration Reaction for the Synthesis of N,N ′-Bicyclic Pyrazolidinone Disulfides

Younan Wang, Yuan Wang, Jingyu Wang, Weiguo Wang
article en

Abstract

A series of <i>N,N</i>'-bicyclic pyrazolidinone disulfides were prepared via a copper(I)-catalyzed interrupted CuAIAC/disulfuration cascade reaction. This protocol proceeded through a copper(I)-catalyzed azomethine imine-alkyne cycloaddition, followed by the interception of the in situ-formed cuprate-pyrazolidinonate intermediate with trisulfide dioxides. The reaction exhibits complete regioselectivity, mild conditions, and broad functional group compatibility, including halogen, cyano, and heterocycle, making it a highly efficient synthetic strategy.

The Journal of Organic ChemistryVol. 91(5)
Qufu Normal University (CN), Alliance for Excellent Education (US)
Clean water and sanitation
Openalex Percentile: Top 81%
Sulfur-Based Synthesis Techniques
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