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Synthesis 1995; 1995(7): 801-804
DOI: 10.1055/s-1995-4002
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Ytterbium(III) Triflate Catalyzed Synthesis of Quinoline Derivatives from N-Arylaldimines and Vinyl Ethers

Yoshikazu Makioka, Takaaki Shindo, Yuki Taniguchi, Ken Takaki* , Yuzo Fujiwara
  • *Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 724, Japan, Fax +81(824)227191
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Publication Date:
31 December 2000 (online)

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[4+2] Cycloaddition reaction of N-arylaldimines with vinyl ethers is effectively catalyzed by ytterbium(III) triflate to give quinoline derivatives in good yields. Furthermore, the reaction with silyl enol ethers affords 4-siloxytetrahydroquinolines, whereas an imino aldol reaction takes place in the reaction with ketene silyl acetals.

quinoline - ytterbium(III) triflate - [4+2] cycloaddition - N-arylaldimine - vinyl ether