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IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines

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    IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
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    • Peng Gao*
      Peng Gao
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. China
      *Email: [email protected]
      More by Peng Gao
      Orcidhttp://orcid.org/0000-0003-1292-0691
    • Huai-Juan Chen
      Huai-Juan Chen
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Huai-Juan Chen
    • Zi-Jing Bai
      Zi-Jing Bai
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Zi-Jing Bai
    • Mi-Na Zhao
      Mi-Na Zhao
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Mi-Na Zhao
      Orcidhttp://orcid.org/0000-0001-7937-9284
    • Desuo Yang
      Desuo Yang
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Desuo Yang
      Orcidhttp://orcid.org/0000-0002-7190-3122
    • Juan Wang*
      Juan Wang
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      *Email: [email protected]
      More by Juan Wang
    • Ning Wang
      Ning Wang
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Ning Wang
    • Lele Du
      Lele Du
      Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China
      More by Lele Du
    • Zheng-Hui Guan*
      Zheng-Hui Guan
      Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, P. R. China
      *Email: [email protected]
      More by Zheng-Hui Guan
      Orcidhttp://orcid.org/0000-0003-4901-5951
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2020, 85, 12, 7939–7951
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    https://doi.org/10.1021/acs.joc.0c00625
    Published May 22, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.0c00625.

    • Detail preparation procedure, characterization data of substrates, and copies of NMR spectra (PDF)

    • X-ray crystallographic structure of 2a (CIF)

    • X-ray crystallographic structure of 4k (CIF)

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    Cited By

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    This article is cited by 23 publications.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2020, 85, 12, 7939–7951
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.0c00625
    Published May 22, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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