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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

Abstract

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.

Keywords

Excellent Yield Nitro Compound Reductive Cyclization Electrolysis Reaction High Reduction Potential 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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