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Multicomponent Synthesis of Imidazo[1,2-a]pyridines: Aerobic Oxidative Formation of C–N and C–S Bonds by Flavin–Iodine-Coupled Organocatalysis

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2020, 22, 20, 8002-8006
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    Multicomponent Synthesis of Imidazo[1,2-a]pyridines: Aerobic Oxidative Formation of C–N and C–S Bonds by Flavin–Iodine-Coupled Organocatalysis
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    • Hayaki Okai
      Hayaki Okai
      Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan
      More by Hayaki Okai
    • Kazumasa Tanimoto
      Kazumasa Tanimoto
      Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan
      More by Kazumasa Tanimoto
    • Ryoma Ohkado
      Ryoma Ohkado
      Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan
      More by Ryoma Ohkado
    • Hiroki Iida*
      Hiroki Iida
      Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan
      *Email: [email protected]
      More by Hiroki Iida
      Orcidhttp://orcid.org/0000-0002-7114-0364
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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 20, 8002–8006
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    https://doi.org/10.1021/acs.orglett.0c02929
    Published October 2, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Herein, we report an aerobic oxidative C–N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.

    Copyright © 2020 American Chemical Society

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    Cited By

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    This article is cited by 40 publications.

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    36. Vishal Srivastava, Pravin K. Singh, Arjita Srivastava, Praveen P. Singh. Synthetic applications of flavin photocatalysis: a review. RSC Advances 2021, 11 (23) , 14251-14259. https://doi.org/10.1039/D1RA00925G
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    39. Jeanese C. Badenock. Six-membered ring systems: pyridines and benzo derivatives. 2021, 341-379. https://doi.org/10.1016/B978-0-323-98410-2.00012-6
    40. Qi Chen, Sihong Chen, Hanqing Wu, Xiaoqing Zeng, Weiqing Chen, Guoxing Sun, Zhaoyang Wang. Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles. Chinese Journal of Organic Chemistry 2021, 41 (9) , 3482. https://doi.org/10.6023/cjoc202104011
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    Organic Letters

    Cite this: Org. Lett. 2020, 22, 20, 8002–8006
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.0c02929
    Published October 2, 2020
    Copyright © 2020 American Chemical Society
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