Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes

Org Lett. 2011 Aug 5;13(15):4136-9. doi: 10.1021/ol2016803. Epub 2011 Jul 11.

Abstract

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.

Publication types

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

MeSH terms

  • Acridones / chemical synthesis*
  • Alkylation
  • Amination
  • Azirines / chemical synthesis
  • Hydrazones / chemistry*
  • Ketones / chemical synthesis*
  • Methylation
  • Molecular Structure

Substances

  • Acridones
  • Azirines
  • Hydrazones
  • Ketones