Format

Send to

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

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

Author information

1
China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science and Technology , Tianjin 300457, China.
2
The Research Centre of Modern Analysis Technology, Tianjin University of Science and Technology , Tianjin 300457, China.

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.

PMID:
28952306
DOI:
10.1021/acs.joc.7b02063

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center