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Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons

Cite this: Org. Lett. 2022, 24, 48, 8859–8863
Publication Date (Web):November 28, 2022
https://doi.org/10.1021/acs.orglett.2c03648
Copyright © 2022 American Chemical Society

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    Abstract

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    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.

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    Cited By

    This article is cited by 3 publications.

    1. 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
    2. 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
    3. 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

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