Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones

Org Lett. 2013 Mar 15;15(6):1282-5. doi: 10.1021/ol400223d. Epub 2013 Feb 22.

Abstract

An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction-cyclization-rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H2 (1 atm) in the presence of Pd/C, 4-quinolones were obtained in excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Cyclopropanes / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Ruthenium / chemistry*

Substances

  • Cyclopropanes
  • Furans
  • Heterocyclic Compounds, 3-Ring
  • Ketones
  • Quinolines
  • Ruthenium