Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4

Org Biomol Chem. 2012 Aug 7;10(29):5643-6. doi: 10.1039/c2ob25767j. Epub 2012 Jun 25.

Abstract

A facile and efficient synthesis of substituted quinolin-2(1H)-ones is developed via intramolecular cyclization of penta-2,4-dienamides mediated by concentrated H(2)SO(4) (98%), and a mechanism involving the formation of a dicationic superelectrophile, and subsequent intramolecular nucleophilic cyclization reactions is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Amides / chemistry*
  • Cyclization
  • Quinolones / chemical synthesis
  • Quinolones / chemistry*
  • Stereoisomerism
  • Sulfuric Acids / chemistry*

Substances

  • Alkadienes
  • Amides
  • Quinolones
  • Sulfuric Acids
  • sulfuric acid