Synthesis of polysubstituted 1,2-dihydroquinolines and indoles via cascade reactions of arylamines and propargylic alcohols catalyzed by FeCl3·6H2O

Org Biomol Chem. 2016 Feb 28;14(8):2515-21. doi: 10.1039/c5ob02658j.

Abstract

An efficient, environmentally friendly and high-yielding route from inexpensive starting materials to 1,2-dihydroquinolines has been developed. This procedure proceeded via a cascade Friedel-Crafts-type reaction and 6-endo-trig hydroamination under the catalysis of FeCl3·6H2O, involving the formation of two new σ (C-C and C-N) bonds in a single operation for the construction of a 1,2-dihydroquinoline skeleton in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Ferric Compounds / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Propanols / chemistry*
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Alkynes
  • Amines
  • Chlorides
  • Ferric Compounds
  • Propanols
  • Quinolines
  • propargyl alcohol
  • ferric chloride