Ru(II)-catalyzed selective C-H amination of xanthones and chromones with sulfonyl azides: synthesis and anticancer evaluation

J Org Chem. 2014 Oct 3;79(19):9262-71. doi: 10.1021/jo501709f. Epub 2014 Sep 24.

Abstract

A ketone-assisted ruthenium-catalyzed selective amination of xanthones and chromones C-H bonds with sulfonyl azides is described. The reactions proceed efficiently with a broad range of substrates with excellent functional group compatibility. This protocol provides direct access to 1-aminoxanthones, 5-aminochromones, and 5-aminoflavonoid derivatives known to exhibit potent anticancer activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Azides / chemical synthesis*
  • Azides / chemistry
  • Azides / pharmacology*
  • Catalysis
  • Chromones / chemical synthesis*
  • Chromones / chemistry
  • Chromones / pharmacology*
  • Flavonoids / chemical synthesis*
  • Flavonoids / chemistry
  • Flavonoids / pharmacology*
  • Molecular Structure
  • Ruthenium / chemistry*
  • Xanthones / chemical synthesis*
  • Xanthones / chemistry
  • Xanthones / pharmacology*

Substances

  • Antineoplastic Agents
  • Azides
  • Chromones
  • Flavonoids
  • Xanthones
  • Ruthenium