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Updated: May 6, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Concise copper-catalyzed synthesis of tricyclic biaryl ether-linked aza-heterocyclic ring systems
Paola Mestichelli1, Matthew J Scott, Warren R J D Galloway
1Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K. , and AstraZeneca , Pharmaceutical Development, Charter Way, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, U.K.
Abstract:
A new method for the synthesis of tricyclic biaryl ether-linked ring systems incorporating seven-, eight-, and nine-membered ring amines is presented. In the presence of catalytic quantities of copper(I), readily accessible acyclic precursors undergo an intramolecular carbon-oxygen bond-forming reaction facilitated by a "templating" chelating nitrogen atom. The methodology displays a broad substrate scope, is practical, and generates rare and biologically interesting tricyclic heteroaromatic products that are difficult to access by other means.
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