Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates

Org Lett. 2008 Sep 18;10(18):4117-20. doi: 10.1021/ol8016726. Epub 2008 Aug 23.

Abstract

A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium-catalyzed borylation of the corresponding o-bromoanilines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Palladium / chemistry
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Boronic Acids
  • Quinolines
  • 3-aminobenzeneboronic acid
  • Palladium