Preparation of optically enriched 3-hydroxy-3,4-dihydroquinolin-2(1H)-ones by heterogeneous catalytic cascade reaction over supported platinum catalyst

György Szollosi, Zsolt Makra, Lenke Kovács, Ferenc Fülöp, Mihály Bartók

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16 Citations (Scopus)

Abstract

The development of a novel heterogeneous catalytic asymmetric cascade reaction for the synthesis of tetrahydroquinolines from 2-nitrophenylpyruvates is reported. Optically enriched 3-hydroxy-3,4-dihydroquinolin-2(1H)-ones are prepared by enantioselective hydrogenation of the activated keto group over a Cinchona alkaloid-modified Pt catalyst, reduction of the nitro group and spontaneous cyclization cascade. Acceleration of the enantioselective hydrogenation of the activated keto group over the catalyst modified by Cinchona alkaloids ensured high tetrahydroquinolinone selectivities. The scope of the reaction was checked using twelve substrates. Both yields and enantioselectivities were significantly influenced by the nature and position of the substituents on the phenyl ring. Substituents adjacent to the nitro group considerably increased the product yield, due to their effect on the nitro group′s reduction rate; however, had only a limited effect on enantioselectivities.

Original languageEnglish
Pages (from-to)1623-1629
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number8
DOIs
Publication statusPublished - May 17 2013

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Keywords

  • Cinchona alkaloids
  • asymmetric synthesis
  • cascade reactions
  • enantioselective hydrogenation
  • heterogeneous catalysis
  • hydroquinolones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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