Concise copper-catalyzed synthesis of tricyclic biaryl ether-linked aza-heterocyclic ring systems

Org Lett. 2013 Nov 1;15(21):5448-51. doi: 10.1021/ol4025259. Epub 2013 Oct 17.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Molecular Structure

Substances

  • Aza Compounds
  • Ethers
  • Heterocyclic Compounds, 3-Ring
  • Copper