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Copper(I)-Catalyzed Synthesis of Functionalized Indolizinones from Substituted Pyridine Homologated Ynones

  • Sushree Ranjan Sahoo
    Sushree Ranjan Sahoo
    Organic Synthesis and Molecular Engineering Laboratory, Department of Chemistry, National Institute of Technology, Rourkela 769008, India
  • Debayan Sarkar*
    Debayan Sarkar
    Organic Synthesis and Molecular Engineering Laboratory, Department of Chemistry, National Institute of Technology, Rourkela 769008, India
    *E-mail: [email protected]
  • Felix Henkel
    Felix Henkel
    Institute of Chemistry of New Materials, University of Osnabrück, Barbarastraβe-6, Osnabrück 49076, Germany
    More by Felix Henkel
  • , and 
  • Hans Reuter
    Hans Reuter
    Institute of Chemistry of New Materials, University of Osnabrück, Barbarastraβe-6, Osnabrück 49076, Germany
    More by Hans Reuter
Cite this: J. Org. Chem. 2020, 85, 2, 902–911
Publication Date (Web):December 23, 2019
https://doi.org/10.1021/acs.joc.9b02853
Copyright © 2019 American Chemical Society

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    Abstract

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    An efficient two-component copper-catalyzed cyclization cascade approach toward highly functionalized indolizinone heterocycles has been developed from reactions of pyridine-, isoquinoline-, and quinoline ynones, via 5-exo-dig cyclization. The catalysis involves the activation by diorgano diselenide and diorgano disulfide and also their incorporation into the indolizinone core. In addition, the obtained substituted indolizinones were readily transformed into 1-(organochalcogenyl)indolizin-2-ols, which are important building blocks in organic synthesis.

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    Cited By

    This article is cited by 12 publications.

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    2. Helen A. Goulart, Ricardo H. Bartz, Thiago J. Peglow, Angelita M. Barcellos, Rodrigo Cervo, Roberta Cargnelutti, Raquel G. Jacob, Eder J. Lenardão, Gelson Perin. Synthesis of Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones by Radical Cyclization of Biaryl Ynones. The Journal of Organic Chemistry 2022, 87 (6) , 4273-4283. https://doi.org/10.1021/acs.joc.1c03112
    3. Yahui Li, Wei Xiong, Zhifeng Zhang, Tongyu Xu. Synthesis of Indolizine Derivatives Triggered by the Oxidative Addition of Aroyl Chloride to Pd(0) Complex. The Journal of Organic Chemistry 2020, 85 (10) , 6392-6399. https://doi.org/10.1021/acs.joc.0c00161
    4. Sushree Ranjan Sahoo, Khushboo Gupta, Vinod K. Singh. Enantioselective Dearomative [4+2] Cycloaddition Reaction of 1‐Naphthols with In‐Situ Generated ortho ‐Quinone Methides. Chemistry – A European Journal 2023, 29 (69) https://doi.org/10.1002/chem.202302707
    5. Maxim V. Musalov, Vladimir A. Potapov, Maria V. Musalova, Svetlana V. Amosova, Leonid B. Krivdin. Recent Developments in the Synthesis of Organoselenium Compounds Based on the Reactions of Organic Diselenides with Acetylenes. Catalysts 2023, 13 (10) , 1369. https://doi.org/10.3390/catal13101369
    6. Xiang Liu, Xiaotian Shi, Jinlei Zhou, Changfeng Huang, Yu Lin, Chen Zhang, Hua Cao. Dearomative cyclization of pyridines/isoquinolines with cyclopropenones: access to indolizinones and benzo-fused indolizinones. Chemical Communications 2023, 59 (27) , 4051-4054. https://doi.org/10.1039/D3CC00492A
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