RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Late-Stage C–H Functionalization of Nimesulide via (Nimesulide)(3,5-Dimethyl-4-Isoxazoly)Jodonium Salt Formation

PII
S3034630425070114-1
DOI
10.7868/S3034630425070114
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 7
Pages
899-906
Abstract
The reaction of N-methylated Nimesulide with Koiser’s reagent based on 4-iodo-3,5-dimethylisoxazole (DMIX-I(OH)OTs) yielded the corresponding iodonium salt. The interaction of this salt with S, O, and N-nucleophiles resulted in the production of functionalized derivatives of Nimesulide.
Keywords
соли диарилиодония функционализация на поздней стадии реакции без использования переходных металлов сульфоны
Date of publication
01.07.2025
Year of publication
2025
Number of purchasers
0
Views
25

References

  1. 1. Guillemard L., Kaplaneris N., Ackermann L., Johansson M.J., Nat. Rev. Chem., 2021, 5, 522. https://doi.org/10.1038/s41570-021-00300-6
  2. 2. Castellino N.J., Montgomery A.P., Danon J.J., Kassiou M., Chem. Rev., 2023, 123, 8127. https://doi.org/10.1021/acs.chemrev.2c00797
  3. 3. Shim S.Y., Chem. Eur. J., 2023, 29, e202302620. https://doi.org/10.1002/chem.202302620
  4. 4. Wang Y., Dana S., Long H., Xu Y., Li Y., Kaplaneris N., Ackermann L., Chem. Rev., 2023, 123, 11269. https://doi.org/10.1021/acs.chemrev.3c00158
  5. 5. Cannalire R., Pelliccia S., Sancineto L., Novellino E., Tron G.C., Giustiniano M., Chem. Soc. Rev., 2021, 50, 766. https://doi.org/10.1039/D0CS00493F
  6. 6. Volkov A.A., Bugaenko D.I., Karchava A.V., ChemCatChem, 2024, 16, e202301526. https://doi.org/10.1002/cctc.202301526
  7. 7. Wu X., Gao P., Chen F., Eur. J. Org. Chem., 2023, 26, e202300864. https://doi.org/10.1002/ejoc.202300864
  8. 8. Timmann S., Feng Z., Alcarazo M., Chem. Eur. J., 2024, 30, e202402768. https://doi.org/10.1002/chem.202402768
  9. 9. Meng H., Liu M.-S., Shu W., Chem. Sci., 2022, 13, 13690. https://doi.org/10.1039/D2SC04507A
  10. 10. Juliá F., Shao Q., Duan M., Plutschack M.B., Berger F., Mateos J., Lu C., Xue X.-S., Houk K.N., Ritter T., J. Am. Chem. Soc., 2021, 143, 16041. https://doi.org/10.1021/jacs.1c06281
  11. 11. Pentsak E.O., Eremin D.B., Gordeev E.G., Anani-kov V.P., ACS Catal., 2019, 9, 3070. https://doi.org/10.1021/acscatal.9b00294
  12. 12. Beletskaya I.P., Ananikov V.P., Chem. Rev., 2022, 122, 16110. https://doi.org/10.1021/acs.chemrev.1c00836
  13. 13. Dohi T., Elboray E.E., Kikushima K., Morimoto K., Kita Y., Chem. Rev., 2025, 125, 3440. https://doi.org/10.1021/acs.chemrev.4c00808
  14. 14. Mamgain R., Sakthivel K., Singh F.V., Beilstein J. Org. Chem., 2024, 20, 2891. https://doi.org/10.3762/bjoc.20.243
  15. 15. Bugaenko D.I., Karchava A.V., Adv. Synth. Catal., 2023, 365, 1893. https://doi.org/10.1002/adsc.202300351
  16. 16. Bugaenko D.I., Volkov A.A., Karchava A.V., J. Org. Chem., 2023, 88, 9968. https://doi.org/10.1021/acs.joc.3c00734
  17. 17. Bugaenko D.I., Tikhanova O.A., Andreychev V.V., Karchava A.V., J. Org. Chem., 2024, 89, 9923. https://doi.org/10.1021/acs.joc.4c00768
  18. 18. Bugaenko D.I., Volkov A.A., Andreychev V.V., Karchava A.V., Org. Lett., 2023, 25, 272. https://doi.org/10.1021/acs.orglett.2c04143
  19. 19. Bugaenko D.I., Malashchenko N.A., Kopytov S.O., Lukonina N.S., Karchava A.V., Org. Lett., 2024, 26, 3189. https://doi.org/10.1021/acs.orglett.4c00797
  20. 20. Chen Y., Gu Y., Meng H., Shao Q., Xu Z., Bao W., Gu Y., Xue X.S., Zhao Y., Angew. Chem. Int. Ed., 2022, 61, e202201240. https://doi.org/10.1002/anie.202201240
  21. 21. Meher P., Panda S.P., Mahapatra S.K., Thombare K.R., Roy L., Murarka S., Org. Lett., 2023, 25, 8290. https://doi.org/10.1021/acs.orglett.3c03365
  22. 22. McCammant M.S., Thompson S., Brooks A.F., Krska S.W., Scott P.J.H., Sanford M.S., Org. Lett., 2017, 19, 3939. https://doi.org/10.1021/acs.orglett.7b01902
  23. 23. Hu C., Jia Q., Bao W., Gu G., Li Y., Zhao Y., Org. Lett., 2024, 26, 7864. https://doi.org/10.1021/acs.orglett.4c02703
  24. 24. Zhou J., Bao Z., Wu P., Chen C., Molecules, 2021, 26, 3240. https://doi.org/10.3390/molecules26113240
  25. 25. Zhou J., Bao Z., Wu P., Chen C., Synthesis, 2022, 54, 1388. https://doi.org/10.1055/a-1679-7753
  26. 26. Bugaenko D.I., Karchava A.V., Adv. Synth. Catal., 2022, 364, 2248. https://doi.org/10.1002/adsc.202200309
  27. 27. Bugaenko D.I., Volkov A.A., Livantsov M.V., Yurovskaya M.A., Karchava A.V., Chem. Eur. J., 2019, 25, 12502. https://doi.org/10.1002/chem.201902955
  28. 28. Seidl T.L., Sundalam S.K., McCullough B., Stuart D.R., J. Org. Chem., 2016, 81, 1998. https://doi.org/10.1021/acs.joc.5b02833
  29. 29. Hatton J., Stuart D.R., Org. Lett., 2025, 27, 1130. https://doi.org/10.1021/acs.orglett.4c04582
  30. 30. Umierski N., Manolikakes G., Org. Lett., 2013, 15, 188. https://doi.org/10.1021/ol303248h
  31. 31. Parida S.K., Jaiswal S., Singh P., Murarka S., Org. Lett., 2021, 23, 6401. https://doi.org/10.1021/acs.orglett.1c02220
  32. 32. Reitti M., Villo P., Olofsson B., Angew. Chem. Int. Ed., 2016, 128, 9074. https://doi.org/10.1002/ange.201603175
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