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Updated: Nov 20, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
An Intramolecular Schmidt Reaction of δ-Azido N-Acylbenzotriazoles
Chun-Fang Liu1, Zhi-Qi Cao1, Shao-Lei Ding1
1College of Chemistry & Chemical Engineering, Ningxia Engineering and Research Center for Natural Medicines, Ningxia University, Yinchuan 750021, China.
Abstract:
A Lewis acid promoted intramolecular Schmidt reaction of N-acylbenzotriazoles with alkyl azides was designed and realized. The benzotriazole was not only employed as an efficient activator for initiating the Schmidt rearrangement but also used as a powerful terminator for the subsequent nucleophilic trapping of the isocyanate ion and/or N-acyliminium ion from the rearrangement. Thirteen δ-azido N-acylbenzotriazoles were investigated, and the conversion afforded the desired benzotriazole-1-carboxamides and lactams with good to excellent yields.
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