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Synthesis of Thiazole-2(3H)-ones via [3,3]-Sigmatropic Rearrangement/5-exo-dig Cyclization of N-Propargylamines

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2022, 87, 14, 9259-9269
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    Synthesis of Thiazole-2(3H)-ones via [3,3]-Sigmatropic Rearrangement/5-exo-dig Cyclization of N-Propargylamines
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 9259–9269
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    https://doi.org/10.1021/acs.joc.2c00991
    Published June 30, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    An efficient methodology has been developed for the synthesis of both di- and trisubstituted thiazol-2(3H)-ones from N-propargylamines and silver(I) trifluoromethanethiolate (AgSCF3) in good yields. The reaction proceeds via [3,3]-sigmatropic rearrangement/5-exo-dig cyclization of N-propargylamines. The starting material can be easily prepared from the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can be extended for the synthesis of thiozole-2(3H)-thione derivatives, and photophysical properties have been studied for some synthesized compounds.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.2c00991.

    • FAIR data, including the primary NMR FID files, for compounds 1p, 1t, 1af, 1ag, 2a–2k, 2n–2z, 2aa–2ae, 3a–3c (ZIP)

    • HRMS spectra of all new compounds (PDF)

    • Detailed experimental procedure for the synthesis of O18 labeled product and deuterium labeled product 2b and its ESI-MS and 13C NMR spectra, copies of 1H, 13C, and 19F NMR spectra, X-ray crystallographic data of compound 2c (PDF)

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    CCDC 2128166 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

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    This article is cited by 3 publications.

    1. Mingxu Wang, Yuchen Gong, Yaolian Shi, Qihai Zhao, Xiao-Jing Zhao, Ganpeng Li, Yonghui He. A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one. The Journal of Organic Chemistry 2024, Article ASAP.
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    2. Subhamoy Biswas, Anil K. Saikia. Cascade Alkynyl Prins Cyclization and Aza-Michael Reaction: En Route to Regioselective Pyrano- and Isochromenoquinoline Scaffolds. The Journal of Organic Chemistry 2024, 89 (19) , 14454-14471. https://doi.org/10.1021/acs.joc.4c01916
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    3. Bipin Kumar Behera, Pallav Jyoti Arandhara, Bikoshita Porashar, Surjya Kumar Bora, Anil K. Saikia. Base-Promoted [4 + 2] Annulation Reaction of In Situ-Generated Azadienes from N-Propargylamines with Active Methylene Compounds: Access to Highly Functionalized 2-Pyridones. The Journal of Organic Chemistry 2023, 88 (21) , 15041-15059. https://doi.org/10.1021/acs.joc.3c01478
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 9259–9269
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.2c00991
    Published June 30, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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