FeCl3-catalyzed cascade cyclization in one pot: synthesis of ring-fused tetrahydroquinoline derivatives from arylamines and N-substituted lactams

J Org Chem. 2013 Aug 16;78(16):8155-60. doi: 10.1021/jo400979h. Epub 2013 Jul 25.

Abstract

Multiple cross-dehydrogenative-coupling reactions catalyzed by FeCl3 in one pot were developed. Arylamines and N-substituted lactams were reacted, and ring-fused tetrahydroquinoline derivatives were formed by two C-C bonds and one C-N bond formation as well as one C-N bond cleavage. The lactams were also used as solvent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Cyclization
  • Ferric Compounds / chemistry*
  • Lactams / chemistry*
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Amines
  • Chlorides
  • Ferric Compounds
  • Lactams
  • Quinolines
  • 1,2,3,4-tetrahydroquinoline
  • ferric chloride