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Updated: May 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Iodide-Catalyzed Intermolecular Formal (3 + 3) Cycloaddition of Bicyclo[1.1.0]butanes and Amides: Modular Access to
Yan Chen1,2, Yu-Tong Zhou2, Zhuang Ge2
1School of Food and Biological Engineering, Hefei University of Technology, Hefei 230009, P. R. China.
Abstract:
Heterobicyclo[3.1.1]heptanes (HBCHeps) are highly valuable bioisosteres of heteroaromatics. Herein, we report an iodide-catalyzed formal (3 + 3) cycloaddition of bicyclo[1.1.0]butanes with amides, providing modular access to 2-oxa-4-azabicyclo[3.1.1]hept-3-enes.This practical, metal-free method exhibits broad functional group tolerance and enables late-stage diversification of bioactive molecules, offering a versatile platform for constructing sp3-rich pyridine bioisosteres in drug discovery.
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