Synthesis of chromeno[2,3-d]imidazol-9(1H)-ones via tandem reactions of 3-iodochromones with amidines involving copper-catalyzed C-H functionalization and C-O bond formation

Org Lett. 2013 Sep 6;15(17):4508-11. doi: 10.1021/ol401966y. Epub 2013 Aug 14.

Abstract

A novel six-membered heterocyclic skeleton of imidazochromone was prepared via an efficient one-pot reaction including a key step of copper-catalyzed aerobic C-H intramolecular cycloetherification. Notably, this process does not require the presence of strong para electron-withdrawing groups on the phenol component. Also, the results of this effort show that acyl phenols containing electron-rich heterocycles participate in an efficient C-H activation/C-O formation process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemistry
  • Catalysis
  • Chromones / chemistry*
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Imidazoles / chemistry*
  • Molecular Structure
  • Phenol / chemistry

Substances

  • Amidines
  • Chromones
  • Heterocyclic Compounds, 3-Ring
  • Imidazoles
  • Phenol
  • Copper