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Updated: Oct 12, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Tandem Amination/Oxetane Ring Opening toward Benzomorpholines
Lindsey G DeRatt1, Chao-Yuan Wang1, Scott D Kuduk1
1Janssen Research and Development, 1400 McKean Road, Spring House, Pennsylvania 19477, United States.
Abstract:
Herein, a tandem approach that allows rapid access to the benzomorpholine scaffold is reported. This operationally simple method allows for valuable heterocycles to be isolated in moderate to high yields. The overall transformation consists of an initial C-N coupling, demonstrated using traditional Ullmann or Buchwald-Hartwig conditions, followed by an in situ oxetane ring opening. A range of functionality is tolerated on the aryl ring, and the cyclization exposes a pendant hydroxymethyl substituent, providing opportunities for further functionalization.
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