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Two-Step Formation of Substituted Pyridines from Iodoenones

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2025, 90, 1, 580-584
    Article

    Two-Step Formation of Substituted Pyridines from Iodoenones
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    • Carl Malenfant
      Carl Malenfant
      Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8 Canada
      More by Carl Malenfant
    • Maxime Denis
      Maxime Denis
      Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8 Canada
      More by Maxime Denis
    • Sylvain Canesi*
      Sylvain Canesi
      Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8 Canada
      *E-mail: [email protected]
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      Orcidhttps://orcid.org/0000-0002-0639-7796
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 1, 580–584
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    https://doi.org/10.1021/acs.joc.4c02502
    Published December 13, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    A new access to substituted pyridines was developed from iodoenones. This two-step procedure involves a Sonogashira coupling with a free alkyne containing a nosylamide followed by a thiophenol treatment in basic conditions that triggers nosyl deprotection, a Michael–retro-Michael process, condensation, and isomerization in cascade to yield the heterocycle. This method enables the introduction of different substituents at several pyridine positions. This approach offers new synthetic opportunities to produce heterocycles present in many bioactive compounds.

    Copyright © 2024 American Chemical Society

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    • 1H and 13C NMR spectral data of all compounds (PDF)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 1, 580–584
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02502
    Published December 13, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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