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Synthesis of Nitrogen-Containing Heterocycles via Imidoyl or Iminyl Radical Intermediates

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Free-Radical Synthesis and Functionalization of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 54))

Abstract

Synthesis of nitrogen-containing heterocycles with isocyanides, isothiocyanates, nitriles, imines, oxime derivatives, and other related compounds has been deeply investigated in organic synthesis. This chapter mainly focuses on summarizing radical cyclization reactions of these C-N unsaturated precursors to afford N-heterocycles in the past decade as well as some earlier feature examples. In most cases, imidoyl or iminyl radicals are involved in cyclizing onto unsaturated systems or heteroatoms to generate N-heterocycles, such as phenanthridines, (iso)quinolines, pyridines, indoles, and pyrroles. A few examples via other types of radical intermediates starting from isothiocyanates, isocyanates, and analogous structures are also included.

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Authors and Affiliations

  1. College of Chemical Engineering and Materials Science, Quanzhou Normal University, Quanzhou, P. R. China

    Jian Lei

  2. Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, P. R. China

    Dengke Li & Qiang Zhu

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  1. Jian Lei
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  2. Dengke Li
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  3. Qiang Zhu
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Correspondence to Jian Lei .

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  1. University of Bordeaux, Talence, France

    Yannick Landais

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Lei, J., Li, D., Zhu, Q. (2017). Synthesis of Nitrogen-Containing Heterocycles via Imidoyl or Iminyl Radical Intermediates. In: Landais, Y. (eds) Free-Radical Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 54. Springer, Cham. https://doi.org/10.1007/7081_2017_9

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