Chemical and Electrochemical Reductive Cyclizations of O-Nitroarenes Toward Nitrogen Containing Heterocycles

  • Byeong Hyo Kim
  • Yoon Seok Lee
  • Yong Rack Choi
  • Sun Kyong Kim
  • Young Moo Jun
  • Woonphil Baik
Conference paper


A series of o-nitroarenes such as 2-nitrobenzaldehydes, 2’-nitroacetophenone, N-(2nitrobenzylidene)anilines, or 2-nitrophenylazobenzenes was examined for reductive cyclizations by applying 2-bromo-2-nitropropane/Zn, SmI2, or cathodic electrolysis. Chemical or electrochemical reactions of o-nitroarenes involving electron transfer processes were found to give heterocycles such as 2,1-benzisoxazoles, or benzotriazoles in excellent yields. Electrolysis of 2-nitrophenylazobenzenes produced benzotriazole N-oxides or benzotriazoles exclusively depending upon the reaction condition.


Excellent Yield Nitro Compound Reductive Cyclization Electrolysis Reaction High Reduction Potential 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Byeong Hyo Kim
    • 2
  • Yoon Seok Lee
    • 1
  • Yong Rack Choi
    • 1
  • Sun Kyong Kim
    • 1
  • Young Moo Jun
    • 1
  • Woonphil Baik
    • 2
  1. 1.Department of ChemistryKwangwoon UniversitySeoulKorea
  2. 2.Department of ChemistryMyong Ji UniversityKyung Ki DoKorea

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