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Synthesis of β-triazolyl sulfones via the reaction of vinyl sulfones with 1,2,4-triazoles under basic conditions

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Abstract

A method was developed for the synthesis of β-triazolyl sulfones from vinylsulfones and 1,2,4-triazoles in the presence of sodium triazolide taken as the base. The reaction was carried out in DMSO at room temperature for 120 h. The target compounds were obtained in 25–89% yields.

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References

  1. S. Kumar, S. L. Khokra, A. Yadav, Futur. J. Pharm. Sci., 2021, 7, 106; DOI: https://doi.org/10.1186/s43094-021-00241-3.

    Article  Google Scholar 

  2. E. A. Chugunova, A. S. Gazizov, A. R. Burilov, L. M. Yusupova, M. A. Pudovik, O. G. Sinyashin, Russ. Chem. Bull., 2019, 68, 887–910; DOI: https://doi.org/10.1007/s11172-019-2503-6.

    Article  CAS  Google Scholar 

  3. I. S. Ryzhkina, L. I. Murtazina, L. A. Kostina, I. S. Dokuchaeva, T. V. Kuznetsova, A. M. Petrov, A. I. Konovalov, Russ. Chem. Bull., 2021, 70, 1499–1508; DOI: https://doi.org/10.1007/s11172-021-3245-9.

    Article  CAS  Google Scholar 

  4. Y. Shi, C. H. Zhou, Bioorg. Med. Chem. Lett., 2011, 21, 956–960; DOI: https://doi.org/10.1016/j.bmcl.2010.12.059.

    Article  CAS  Google Scholar 

  5. R. Paprocka, M. Wiese, A. Eljaszewicz, A. Helmin-Basa, A. Gzella, B. Modzelewska-Banachiewicz, J. Michalkiewicz, Bioorg. Med. Chem. Lett., 2015, 25, 2664–2667; DOI: https://doi.org/10.1016/j.bmcl.2015.04.079.

    Article  CAS  Google Scholar 

  6. R. Kaur, A. R. Dwivedi, B. Kumar, V. Kumar, Anti-Cancer Agents Med. Chem., 2016, 16, 465–489; DOI: https://doi.org/10.2174/1871520615666150819121106.

    Article  CAS  Google Scholar 

  7. C. H. Zhou, Y. Wang, Curr. Med. Chem., 2012, 19, 239–280; DOI: https://doi.org/10.2174/092986712803414213.

    Article  CAS  Google Scholar 

  8. C. T. Supuran, A. Casini, A. Scozzafava, Med. Res. Rev., 2003, 23, 535–558; DOI: https://doi.org/10.1002/med.10047.

    Article  CAS  Google Scholar 

  9. H. S. Civelek, P. G. Weintraub, Crop Protection, 2003, 22, 479–483; DOI: https://doi.org/10.1016/S0261-2194(02)00197-7.

    Article  CAS  Google Scholar 

  10. A. Regueiro-Ren, in Adv. Heterocycl. Chem., eds. N. A. Meanwell, M. L. Lolli, 2021, 134, 1–30 pp.; DOI: https://doi.org/10.1016/bs.aihch.2020.10.003.

  11. W. M. Wolf, J. Mol. Struct., 1999, 474, 113–124; DOI: https://doi.org/10.1016/S0022-2860(98)00565-1.

    Article  CAS  Google Scholar 

  12. A. Gucalp, S. Tolaney, S. J. Isakoff, J. N. Ingle, M. C. Liu, L. A. Carey, K. Blackwell, H. Rugo, L. Nabell, A. Forero, V. Stearns, A. S. Doane, M. Danso, M. E. Moynahan, L. F. Momen, J. M. Gonzalez, A. Akhtar, D. D. Giri, S. Patil, K. N. Feigin, C. A. Hudis, T. A. Traina, C. Translational Breast Cancer Research, Clin. Cancer Res., 2013, 19, 5505–5512; DOI: https://doi.org/10.1158/1078-0432.CCR-12-3327.

    Article  CAS  Google Scholar 

  13. Y. I. Zhu, M. J. Stiller, J. Am. Acad. Dermatol., 2001, 45, 420–434; DOI: https://doi.org/10.1067/mjd.2001.114733.

    Article  CAS  Google Scholar 

  14. M. A. Abdelgawad, M. B. Labib, W. A. M. Ali, G. Kamel, A. A. Azouz, E. S. El-Nahass, Bioorg. Chem., 2018, 78, 103–114; DOI: https://doi.org/10.1016/j.bioorg.2018.03.011.

    Article  CAS  Google Scholar 

  15. B. Kahveci, F. Yilmaz, E. Menteşe, S. Ülker, Arch. Pharm., 2017, 350, 1600369; DOI: https://doi.org/10.1002/ardp.201600369.

    Article  Google Scholar 

  16. A. O. Terent’ev, O. M. Mulina, D. A. Pirgach, A. I. Ilovaisky, M. A. Syroeshkin, N. I. Kapustina, G. I. Nikishin, Tetrahedron, 2017, 73, 6871–6879; DOI: https://doi.org/10.1016/j.tet.2017.10.047.

    Article  Google Scholar 

  17. F. Liebner, U. Bankwitz, K. Rühlmann, Liebigs Ann. Chem., 1994, 1994, 145–150; DOI: https://doi.org/10.1002/jlac.199419940207.

    Article  Google Scholar 

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Funding

This work was financially supported by the Russian Science Foundation (Grant No. 19-73-20190).

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Correspondence to A. O. Terent’ev.

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Dedicated to Academician of the Russian Academy of Sciences V. I. Ovcharenko on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1544–1548, July, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Radulov, P.S., Mozzhegorov, A.V., Mulina, O.M. et al. Synthesis of β-triazolyl sulfones via the reaction of vinyl sulfones with 1,2,4-triazoles under basic conditions. Russ Chem Bull 71, 1544–1548 (2022). https://doi.org/10.1007/s11172-022-3562-7

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  • DOI: https://doi.org/10.1007/s11172-022-3562-7

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