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Regioselective Photocycloaddition of Saccharin Anion to π-Systems: Continuous-Flow Synthesis of Benzosultams

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    Regioselective Photocycloaddition of Saccharin Anion to π-Systems: Continuous-Flow Synthesis of Benzosultams
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    • Francisco N. Figueroa
      Francisco N. Figueroa
      Departamento de Química Orgánica, Facultad de Ciencias Químicas, UNC-IPQA-CONICET, Ciudad Universitaria, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
      More by Francisco N. Figueroa
    • Adrián A. Heredia
      Adrián A. Heredia
      INFIQC-CONICET-UNC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
      More by Adrián A. Heredia
    • Alicia B. Peñéñory
      Alicia B. Peñéñory
      INFIQC-CONICET-UNC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
      More by Alicia B. Peñéñory
      Orcidhttp://orcid.org/0000-0001-9557-6472
    • Diego Sampedro*
      Diego Sampedro
      Departamento de Química Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, Logroño 26006, Spain
      *E-mail: [email protected] (D.S.).
      More by Diego Sampedro
      Orcidhttp://orcid.org/0000-0003-2772-6453
    • Juan E. Argüello*
      Juan E. Argüello
      INFIQC-CONICET-UNC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
      *E-mail: [email protected] (J.E.A.).
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      Orcidhttp://orcid.org/0000-0002-7321-4291
    • Gabriela Oksdath-Mansilla*
      Gabriela Oksdath-Mansilla
      INFIQC-CONICET-UNC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina
      *E-mail: [email protected] (G.O.M.).
      More by Gabriela Oksdath-Mansilla
      Orcidhttp://orcid.org/0000-0002-8999-3314
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2019, 84, 7, 3871–3880
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.8b02984
    Published March 4, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Saccharin is a versatile scaffold to build up different heterocycles with relevance in asymmetric catalysis, agricultural chemistry, medicinal chemistry, and so forth. Here, we report a photochemical strategy to obtain seven-membered ring benzosultams in one step, using saccharin anion as starting material. The reaction can be improved in a photoflow reactor and its scope was evaluated. Furthermore, computational study at the CASPT2//CASSCF level of theory was also performed to rationalize the involved mechanism.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.8b02984.

    • 1H NMR and 13C NMR for all compounds, continuous photoflow setup, photophysical study, and Cartesian coordinates for the computed structures (PDF)

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    Cited By

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    This article is cited by 17 publications.

    1. Jun-An Xiao, Huan Zhang, Xue-Ling Luo, Ru-Fang Meng, Wei Wang, Wei-dong Lu, Wei Su, Chenxiang Lin, Peng-Ju Xia, Hua Yang. Diastereoselective Access to Seven-Membered Benzosultams via Palladium-Catalyzed Ring-Opening [3 + 2]-Annulation. Organic Letters 2023, 25 (22) , 4145-4149. https://doi.org/10.1021/acs.orglett.3c01422
    2. Raushan Kumar Jha, Monojit Batabyal, Sangit Kumar. Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(sp2)–H and N–H Bonds: Amination of Naphthoquinones with Amines. The Journal of Organic Chemistry 2023, 88 (11) , 7401-7424. https://doi.org/10.1021/acs.joc.3c00666
    3. Laura Buglioni, Fabian Raymenants, Aidan Slattery, Stefan D. A. Zondag, Timothy Noël. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry. Chemical Reviews 2022, 122 (2) , 2752-2906. https://doi.org/10.1021/acs.chemrev.1c00332
    4. Zi-Qi Zhang, Yi-Hao Xu, Jing-Cheng Dai, Yan Li, Jie Sheng, Xi-Sheng Wang. Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines. Organic Letters 2021, 23 (6) , 2194-2198. https://doi.org/10.1021/acs.orglett.1c00344
    5. Andrey N. Komogortsev, Valeriya G. Melekhina, Boris V. Lichitskii. Anionic photochemical rearrangement of 3-hydroxypyran-4-ones bearing oxazol-2-one fragment. Organic & Biomolecular Chemistry 2024, 22 (8) , 1686-1692. https://doi.org/10.1039/D3OB01957H
    6. Dawid Drelinkiewicz, Stephen T. Alston, Thomas Durand, Richard J. Whitby. The switch-off method: rapid investigation of flow photochemical reactions. Reaction Chemistry & Engineering 2023, 8 (9) , 2134-2140. https://doi.org/10.1039/D3RE00261F
    7. Yuanyuan Ping, Xiao Li, Qi Pan, Wangqing Kong. Ni‐Catalyzed Divergent Synthesis of 2‐Benzazepine Derivatives via Tunable Cyclization and 1,4‐Acyl Transfer Triggered by Amide N‐C Bond Cleavage. Angewandte Chemie 2022, 134 (25) https://doi.org/10.1002/ange.202201574
    8. Yuanyuan Ping, Xiao Li, Qi Pan, Wangqing Kong. Ni‐Catalyzed Divergent Synthesis of 2‐Benzazepine Derivatives via Tunable Cyclization and 1,4‐Acyl Transfer Triggered by Amide N‐C Bond Cleavage. Angewandte Chemie International Edition 2022, 61 (25) https://doi.org/10.1002/anie.202201574
    9. Sören Holtwick, Thomas J.J. Müller. 1,2-Oxazepines and 1,2-Thiazepines. 2022, 269-312. https://doi.org/10.1016/B978-0-12-818655-8.00076-7
    10. Yulia N. Toikka, Dar’ya V. Spiridonova, Alexander S. Novikov, Nadezhda A. Bokach. Copper(II) Prevents the Saccarine-Dialkylcyanamide Coupling by Forming Mononuclear (Saccharinate)(Dialkylcyanamide)copper(II) Complexes. Inorganics 2021, 9 (9) , 69. https://doi.org/10.3390/inorganics9090069
    11. Hassan Seyrani, Sorour Ramezanpour, Aref Vaezghaemi, Farzad Kobarfard. A sequential Ugi–Smiles/transition-metal-free endo -dig Conia–ene cyclization: the selective synthesis of saccharin substituted 2,5-dihydropyrroles. New Journal of Chemistry 2021, 45 (34) , 15647-15654. https://doi.org/10.1039/D1NJ01159F
    12. Vasyl Y. Hys, Demyd S. Milokhov, Tetiana Ye. Keda, Iryna V. Omelchenko, Irina S. Konovalova, Svitlana V. Shishkina, Yulian M. Volovenko. Efficient synthesis of seven-membered Aza-sultams: Heterofused amino-1,2,4-thiadiazepine dioxides. Tetrahedron 2021, 88 , 132149. https://doi.org/10.1016/j.tet.2021.132149
    13. Matthias Schmalzbauer, Michela Marcon, Burkhard König. Photoangeregte Anionen in organischen Reaktionen. Angewandte Chemie 2021, 133 (12) , 6338-6363. https://doi.org/10.1002/ange.202009288
    14. Matthias Schmalzbauer, Michela Marcon, Burkhard König. Excited State Anions in Organic Transformations. Angewandte Chemie International Edition 2021, 60 (12) , 6270-6292. https://doi.org/10.1002/anie.202009288
    15. Adam G. Meyer, Alex C. Bissember, Christopher J.T. Hyland, Charlotte C. Williams, Monika Szabo, Steven M. Wales, Grace E.O. Constable, Wesley J. Olivier. Seven-membered rings. 2021, 565-614. https://doi.org/10.1016/B978-0-323-89812-6.00016-X
    16. Stefan Zimmermann, Mohammad Akbarzadeh, Felix Otte, Carsten Strohmann, Muthukumar Gomathi Sankar, Slava Ziegler, Axel Pahl, Sonja Sievers, Kamal Kumar. A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides. Chemistry – A European Journal 2019, 25 (68) , 15498-15503. https://doi.org/10.1002/chem.201904175
    17. Alexey Yu. Dubovtsev, Daniil M. Ivanov, Uladzislava Dabranskaya, Nadezhda A. Bokach, Vadim Yu. Kukushkin. Saccharin guanidination via facile three-component “two saccharins-one dialkylcyanamide” integration. New Journal of Chemistry 2019, 43 (27) , 10685-10688. https://doi.org/10.1039/C9NJ02656H
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2019, 84, 7, 3871–3880
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.8b02984
    Published March 4, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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