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Updated: Feb 20, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of diverse substituted pyrimidines through Cu catalyst-controlled Ts group elimination and reinsertion
Wen Cheng1, Mengfan Li1, Hao Tang1
1School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418, P. R. China. yiwy@sit.edu.cn.
Abstract:
Two copper-controlled reactions of 2H-azirines with TosMICs have been developed that provide two efficient and modular approaches to diverse substituted pyrimidines with non-electron-withdrawing substituents at position 4 or 6. The Ts group of TosMIC plays a dual role as the sulfonyl source and the leaving group in the methodologies. Cascade reaction pathways comprising [3 + 2] cycloaddition, ring expansion, Ts group elimination-aromatization, Ts group reinsertion, and oxidative aromatization are also disclosed.
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