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Keywords:

  • Nitrogen heterocycles;
  • Ruthenium;
  • Oxidative cyclization;
  • Friedländer reaction

Abstract

In a modification of the Friedländer reaction, 2-aminobenzyl alcohol is oxidatively cyclized with a variety of ketones to yield substituted quinolines. Of all the ruthenium catalysts that were tested for this reaction, the second-generation Grubbs' catalyst gives the highest quinoline yield, in combination with KOtBu as a base. The presence of a hydrogen acceptor is required to regenerate the catalyst. Also the reaction mechanism is discussed, and the results show that there are possibly two different pathways towards quinolines.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)