Facile Three-Component Synthesis of Substituted Quinolines Catalyzed by Iridium(III) Complex

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  • Takayuki Nakajima
    Department of Applied Chemistry, Graduate School of Science and Engineering, Waseda University
  • Takashi Inada
    Department of Applied Chemistry, Graduate School of Science and Engineering, Waseda University
  • Takeyuki Igarashi
    Department of Applied Chemistry, Graduate School of Science and Engineering, Waseda University
  • Tadashi Sekioka
    Department of Applied Chemistry, Graduate School of Science and Engineering, Waseda University
  • Isao Shimizu
    Department of Applied Chemistry, Graduate School of Science and Engineering, Waseda University

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<jats:title>Abstract</jats:title> <jats:p>A convenient and efficient synthesis of substituted quinolines via a simple one-pot reaction of an aniline, an aromatic aldehyde, and an enolizable aliphatic aldehyde in the presence of the iridium catalyst [IrCl2H(cod)]2 under oxygen as an oxidant was developed. The reaction proceeds with Mannich-type imine formation followed by nucleophilic addition to give β-amino aldehydes. Dehydrative cyclization takes place to give dihydroquinoline, which is then dehydrogenated by aerobic oxidation to give 2-aryl-3-alkylquinolines. Dialkylquinolines were obtained by the reaction with anilines and aliphatic aldehydes in good yields.</jats:p>

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