A novel generation of indole-2,3-quinodimethanes

Org Lett. 2006 Apr 27;8(9):1843-5. doi: 10.1021/ol060418n.

Abstract

[reaction: see text] A novel and efficient procedure for the generation of the reactive indole-2,3-quinodimethane intermediates from the allenylanilines is described. The indole-2,3-quinodimethane intermediates were captured by several dienophiles to afford the corresponding tetrahydro- and dihydrocarbazole derivatives. This method is significantly different from the previously reported ones, which involve the 1,4-elimination or its related reactions of the indole derivatives that possess suitable substituents at both the C-2 and C-3 positions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis*
  • Methane / chemistry
  • Molecular Structure

Substances

  • Aniline Compounds
  • Indoles
  • Methane