Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones

J Org Chem. 2012 Jul 20;77(14):6262-70. doi: 10.1021/jo3011073. Epub 2012 Jul 10.

Abstract

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridones / chemical synthesis*
  • Acridones / chemistry
  • Alkynes / chemistry*
  • Ethylenes / chemistry*
  • Molecular Structure
  • Quinolones / chemistry*
  • Stereoisomerism
  • beta-Lactams / chemistry*

Substances

  • Acridones
  • Alkynes
  • Ethylenes
  • Quinolones
  • beta-Lactams
  • ethylene