Synthesis of quinine N-oxide and an NMR tutorial in its structure determination

  • Aisyah Aisyah
  • Nila Berghuis Tamaela
  • Joko Santoso
  • Yana Maolana Syah
  • Didin Mujahidin
Keywords: quinine, oxidation, chemoselective, NMR spectroscopy

Abstract

Cinchona alkaloids are one of abundant natural chiral pool for organocatalysts. The application of an N-oxide group containing molecule in asymmetric reaction is currently wide developed. The structure of quinine consist two amine groups that could be oxidized to the N-oxide groups at N-1’ of quinoline and at N-1 of quinuclidine moieties. The oxidation reaction took place selectively at quinuclidine moiety by controlling the concentration of oxidizing agents. In this study we showed that N-1-oxide quinine could be occurred chemo­selectively by using a low concentration of ozone thana palladium catalyzed oxidation. The structure of products N1-oxide quinine was elucidated by spectroscopy data including 1H-NMR, 13C-NMR, 2D-NMR, infra-red and mass spectrometry. The developed method is a chemoselectively and eco-friendly method for synthesis N1-oxide quinine.

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Published
2016-02-15
Section
Archive