Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles

Org Lett. 2010 Dec 3;12(23):5394-7. doi: 10.1021/ol102027j. Epub 2010 Nov 5.

Abstract

An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azoles / chemical synthesis*
  • Catalysis
  • Copper / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Models, Molecular
  • Molecular Structure
  • Nitrogen / chemistry*
  • Organoselenium Compounds / chemical synthesis*
  • Selenium Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Azoles
  • Heterocyclic Compounds
  • Organoselenium Compounds
  • Selenium Compounds
  • ebselen
  • Copper
  • Nitrogen