American Chemical Society
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Concise Copper-Catalyzed Synthesis of Tricyclic Biaryl Ether-Linked Aza-Heterocyclic Ring Systems

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journal contribution
posted on 2013-11-01, 00:00 authored by Paola Mestichelli, Matthew J. Scott, Warren R. J. D. Galloway, Jamie Selwyn, Jeremy S. Parker, David R. Spring
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.