The ruthenium complex catalyzed N-heterocyclization of aminoarenes to quinoline derivatives using allylic alcohols and aliphatic aldehydes.

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概要

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• Aminoarenes reacted with 2-propen-1-ol and 2-buten-1-ol at 180 °C to give quinoline derivatives in fairly good yields in the presence of a catalytic amount of a ruthenium complex. Dichlorotris(triphenylphosphine)ruthenium was the most effective catalyst. The aminoarenes with electron-releasing groups favored the formation of the quinolines. The <I>N</I>-heterocyclization also proceeded when aliphatic aldehydes were used in place of the allylic alcohols. The employment of allylic alcohols gave, however, higher yields in several cases. The reaction involves the isomerization of the allylic alcohols to the corresponding aldehydes. The aldehydes reacted with aminoarenes to give Schiff-base dimers which were then cyclized in the presence of the ruthenium complex to the quinolines. As a key intermediate in the reaction, the ortho-metallated species has been proposed.

• 公益社団法人 日本化学会の論文

著者

• Tsuji Yasushi

  Department Of Energy And Hydrocarbon Chemistry Graduate School Of Engineering Kyoto University

• Watanabe Yoshihisa

  Department Of Basic Geriatrics Graduate School Of Medical Science Kyoto Prefectural University Of Medicine

• Ohsugi Yukihiro

  Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University

• Shida Jun

  Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University

• Tsuji Yasushi

  Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University

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