Access to 8-Azachromones via Activation of C-H in N-Oxides

J Org Chem. 2017 Oct 20;82(20):11275-11287. doi: 10.1021/acs.joc.7b02063. Epub 2017 Oct 4.

Abstract

A concise and practical synthetic method has been developed for 8-azachromones, including 8-azaflavones, which have emerged as a promising class of compounds. Using commercially available nicotinates as the starting material, 8-azachromones were obtained in only three steps. The key intramolecular O-arylation reaction was achieved by nucleophilic attack of enolates to C2 of N-oxides under PyBrop or Ac2O activation conditions. These studies provide the basis for the access to 8-azachromones, enabling future work including the discovery and development of novel chromonoid drugs or other functional materials.

Publication types

  • Research Support, Non-U.S. Gov't