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Updated: Jan 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A Tandem Strategy: Wolff Rearrangement/Staudinger [2+2] Cycloaddition via Metal Carbenes for the Synthesis of
1Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China.
Abstract:
The spiro[azetidine-3,3'-benzofuran]-2-one motif represents an important yet underexplored class of spirocyclic β-lactams, making the development of an efficient synthetic route to access this scaffold highly desirable. Herein, we report a concise tandem protocol for its synthesis from diazo compounds and imines. This tandem process proceeds through metal carbene formation, Wolff rearrangement, and Staudinger [2+2] cycloaddition to efficiently construct the target spirocyclic β-lactam with high diastereoselectivity. The practicality of this methodology was further demonstrated through a gram-scale synthesis and additional transformations. Notably, the synthesized compounds exhibited potent anti-influenza A virus activity, with an EC50 value as low as 2.39 ± 0.21 μM.
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