PPA-mediated C-C bond formation: a synthetic route to substituted indeno[2,1-c]quinolin-6(7H)-ones

Org Lett. 2013 Feb 15;15(4):776-9. doi: 10.1021/ol303423f. Epub 2013 Feb 7.

Abstract

A facile and efficient synthesis of substituted indeno[2,1-c]quinolin-6(7H)-ones from a variety of α-acyl N-arylcinnamamides mediated by polyphosphoric acid (PPA) is described, and a mechanism involving the formation of a dicationic superelectrophile and subsequent double intramolecular nucleophilic cyclization reactions is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indenes / chemical synthesis*
  • Indenes / chemistry
  • Molecular Structure
  • Phosphoric Acids / chemistry*
  • Polymers / chemistry*
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Indenes
  • Phosphoric Acids
  • Polymers
  • Quinolones
  • polyphosphoric acid