Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based alpha,alpha-amino esters

Org Biomol Chem. 2010 Feb 7;8(3):622-7. doi: 10.1039/b918898c. Epub 2009 Dec 8.

Abstract

An unusual and efficient method for the synthesis of new quinone-based amine and its derivatives from the corresponding alpha,alpha-amino ester is described. The procedure involves the quinone-based system's oxidative decarboxylation via hydride transfer throughout basic hydrolysis. This synthetic method provides, with good yields, rapid access to new potentially cytotoxic quinones.

MeSH terms

  • Amines / chemistry
  • Benzoquinones / chemical synthesis*
  • Benzoquinones / chemistry*
  • Carboxylic Acids / chemistry*
  • Esters / chemistry*
  • Hydrolysis
  • Oxidation-Reduction

Substances

  • Amines
  • Benzoquinones
  • Carboxylic Acids
  • Esters
  • quinone