ACS Publications. Most Trusted. Most Cited. Most Read
Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2022, 24, 48, 8859-8863
    Letter

    Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2022, 24, 48, 8859–8863
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c03648
    Published November 28, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The moiety of 4-imidazolidinone is an important structural motif in organic synthesis and medicinal chemistry. We present the synthesis of 4-imidazolidinones from various diamides with ethynyl benziodoxolones through double Michael-type addition, which is an unprecedented reaction mode for hypervalent alkynyl iodine compounds. cis-2,5-Disubstituted 4-imidazolidinones were diastereoselectively synthesized from amino acid derived diamides. Having derivatized the 4-imidazolidinones, several control experiments and density functional theory calculations were conducted to realize mechanistic insight.

    Copyright © 2022 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.2c03648.

    • Experimental procedures and characterization data (PDF)

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 4 publications.

    1. Takashi Kano, Ryusei Uozumi, Toshifumi Maruyama, Norihiro Tada, Akichika Itoh. Modular Synthesis of Tripeptide Analogs with an Aminobitriazole Skeleton Using Diynyl Benziodoxolone as a Trivalent Platform. The Journal of Organic Chemistry 2024, 89 (16) , 11761-11765. https://doi.org/10.1021/acs.joc.4c00999
    2. Lei Xie, Chenyi Zhao, Zhaoxue Wang, Zirui Chen, Yingying Zhao, Xinghan Liu, Xiangdong Xu, Wanxing Liu, Xiaojing Li, Lingang Wu. Synthesis of Polycyclic Imidazolidinones via Cascade [3 + 2]-Annulation of β-Oxo-acrylamides with Cyclic N-Sulfonyl Imines. The Journal of Organic Chemistry 2023, 88 (22) , 15805-15816. https://doi.org/10.1021/acs.joc.3c01878
    3. Antoine Roblin, Nicolas Casaretto, Alexis Archambeau. Diastereo- and Enantioselective Palladium-Catalyzed Cycloadditions of 5-Vinyloxazolidine-2,4-diones with Electrophilic Imines. Organic Letters 2023, 25 (35) , 6453-6458. https://doi.org/10.1021/acs.orglett.3c01883
    4. Irina A. Mironova, Dmitrii M. Noskov, Akira Yoshimura, Mekhman S. Yusubov, Viktor V. Zhdankin. Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications. Molecules 2023, 28 (5) , 2136. https://doi.org/10.3390/molecules28052136
    Download PDF
    Go to Organic Letters
    Get e-Alerts
    Get e-Alerts

    Organic Letters

    Cite this: Org. Lett. 2022, 24, 48, 8859–8863
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c03648
    Published November 28, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

    Article Views

    1170

    Altmetric

    -

    Citations

    4
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.