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Novel Trends in Electroorganic Synthesis pp 325–328Cite as

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

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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.

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Author information

Authors and Affiliations

  1. Department of Chemistry, Kwangwoon University, Seoul, 139-701, Korea

    Yoon Seok Lee, Yong Rack Choi, Sun Kyong Kim & Young Moo Jun

  2. Department of Chemistry, Myong Ji University, Kyung Ki Do, 449-728, Korea

    Byeong Hyo Kim & Woonphil Baik

Authors
  1. Byeong Hyo Kim
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  2. Yoon Seok Lee
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  3. Yong Rack Choi
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  4. Sun Kyong Kim
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  5. Young Moo Jun
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  6. Woonphil Baik
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Editor information

Editors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushima-naka, 700-8530, Okayama, Japan

    Sigeru Torii

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© 1998 Springer Japan

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Kim, B.H., Lee, Y.S., Choi, Y.R., Kim, S.K., Jun, Y.M., Baik, W. (1998). Chemical and Electrochemical Reductive Cyclizations of O-Nitroarenes Toward Nitrogen Containing Heterocycles. In: Torii, S. (eds) Novel Trends in Electroorganic Synthesis. Springer, Tokyo. https://doi.org/10.1007/978-4-431-65924-2_97

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  • DOI: https://doi.org/10.1007/978-4-431-65924-2_97

  • Publisher Name: Springer, Tokyo

  • Print ISBN: 978-4-431-65926-6

  • Online ISBN: 978-4-431-65924-2

  • eBook Packages: Springer Book Archive

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