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Updated: Jun 9, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized
Bandana Singh1, Pujan Sasmal2, Aaron Taites2
1Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Lucknow 226014, India.
Abstract:
A strategy for activating azabicyclo[1.1.0]butane (ABB) with in situ generated aza-ortho-quinone methide, promoted by HFIP, is reported. This unified activation, vis-à-vis strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the newly installed motif on azetidine nitrogen could be forged into an indoline via Pd-catalyzed hydroamination, leveraging access to medicinally relevant scaffolds.
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