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Updated: Jan 3, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Mild Intramolecular Ring Opening of Oxetanes
Lindsey G DeRatt1, Edward C Lawson1, Chao-Yuan Wang1
1Janssen Research and Development , 1400 McKean Road , Spring House , Pennsylvania 19477 , United States.
Abstract:
Oxetanes have been increasingly used as stable motifs in medicinal chemistry as well as versatile synthetic intermediates. Herein, an intramolecular ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of molecular complexity in a single step from simple, readily available substrates.
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