高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 314.

• Organic Synthesis Chemistry • 上一篇    下一篇

N-Arylimine 1,4-Cycloaddition Reaction. Preparation of Substituted Hexahydrofuro[3,2c] Quinolines from Shiff Bases and 2,3-Dihydrofuran

Jun ZHAO, Shu Feng CHEN, Xiao Tian LIANG   

  1. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050
  • 出版日期:1998-12-31 发布日期:1998-12-31

N-Arylimine 1,4-Cycloaddition Reaction. Preparation of Substituted Hexahydrofuro[3,2c] Quinolines from Shiff Bases and 2,3-Dihydrofuran

Jun ZHAO, Shu Feng CHEN, Xiao Tian LIANG   

  1. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050
  • Online:1998-12-31 Published:1998-12-31

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摘要： The synthesis of nitrogen heterocycles through cycloaddition reaction of imines has stimulated much preparative and mechanistic work. 1,2The reaction of Shiff bases with electro-rich olefins has been utilized for the systhesis of quinoline derivatives. 3This paper introduces Lewis acid catalyzed cycloaddition reactions of N-arylideneaniline(Ⅰ) with 2,3-dihydrofuran(Ⅱ), which gives a pair of epimers dl-2,3,3a,4,5,9b-hexahydro-4-arylfuro[3,2-c]quinolines (Ⅲ and Ⅲ') and a few of their corresponding aromatized compounds.(Ⅳ)

Abstract: The synthesis of nitrogen heterocycles through cycloaddition reaction of imines has stimulated much preparative and mechanistic work. 1,2The reaction of Shiff bases with electro-rich olefins has been utilized for the systhesis of quinoline derivatives. 3This paper introduces Lewis acid catalyzed cycloaddition reactions of N-arylideneaniline(Ⅰ) with 2,3-dihydrofuran(Ⅱ), which gives a pair of epimers dl-2,3,3a,4,5,9b-hexahydro-4-arylfuro[3,2-c]quinolines (Ⅲ and Ⅲ') and a few of their corresponding aromatized compounds.(Ⅳ)

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