N-Sulfurylation of 2-(2-Furyl)- and 2-(2-Furylmethyl)anilines

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The interaction of furyl-substituted anilines with various arylulfonyl chlorides was studied. The reaction proceeds selectively in the case of 2-(2-furyl)anilines. The Hinsberg reaction products formed in the first step undergo repeated spontaneous sulfarylation in the presence of electron-withdrawing groups in the sulfaryl moiety, as clearly confirmed by X-ray diffraction analysis.

About the authors

S. Annadurdyyeva

RUDN University

Moscow, Russia

G. M. Burkin

RUDN University

Moscow, Russia

E. A. Kvyatkovskaya

RUDN University

Moscow, Russia

Liangyue Cheng

RUDN University

Moscow, Russia

V. N. Khrustalev

RUDN University; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Moscow, Russia; Moscow, Russia

P. V. Dorovatovskii

National Research Centre "Kurchatov Institute"

Moscow, Russia

V. P. Zaytsev

RUDN University

Email: zaytsev-vp@rudn.ru
Moscow, Russia

References

  1. Hinsberg O. Ber. Dtsch. Chem. Ges. 1890, 23, 2962–2965. https://doi.org/10.1002/cber.189002302215
  2. Hinsberg O., Kessler J. Ber. Dtsch. Chem. Ges. 1905, 38, 906–911. https://doi.org/10.1002/cber.190503801161
  3. Neipp L., Sackmann W. Tripod, Antibiot. Chemother. 1961, 9, 19–82. https://doi.org/10.1159/000386713
  4. Reitz A.B., Smith G.R., Parker, M.H. Expert Opin. Ther. Pat. 2009, 19, 1449–1453. https://doi.org/10.1517/13543770903185920
  5. Gelmo P. J. Prakt. Chem. 1908, 77, 369–382. https://doi.org/10.1002/prac.19080770129
  6. Yun M.-K., Wu Y., Li Z., Zhao Y., Waddell M.B., Ferreira A.M., Lee R.E., Bashford D., White S.W. Science. 2012, 335, 1110–1114. https://doi.org/10.1126/science.1214641
  7. Zhao Y., Shadrick W.R., Wallace M.J., Wu Y., Griffith E.C., Qi J., Yun M.-K., White S.W., Lee R.E. Bioorg. Med. Chem. Lett. 2016, 26, 3950–3954. https://doi.org/10.1016/j.bmcl.2016.07.006
  8. Nadirova M.A., Khanova A.V., Zubkov F.I., Mertsalov D.F., Kolesnik I.A., Petkevich S.K., Potkin V.I., Shetnev A.A., Presnukhina S.I., Sinelshchikova A.A., Grigoriev M.S., Zaytsev V.P. Tetrahedron. 2021, 85, 132032. https://doi.org/10.1016/j.tet.2021.132032
  9. Logemann W., Giraldi P.N., Parenti M.A. Nature. 1959, 184, 1711. https://doi.org/10.1038/1841711a0
  10. Destevens G., Halamandaris A., Ricca Jr., S., Werner L.H. J. Med. Chem. 1959, 1, 565–576. https://doi.org/10.1021/jm50007a002
  11. Thiry A., Dogne J.-M., Supuran C.T., Masereel B. Curr. Pharm. Des. 2008, 14, 661–671. https://doi.org/10.2174/138161208783877956
  12. Supuran C.T., Casini A., Scozzafava A. Med. Res. Rev. 2003, 23, 535–538. https://doi.org/10.1002/med.10047
  13. Chohan Z.H., Shaikh U., Rauf A., Supuran C.T. J. Enzym. Inhib. Ch. 2006, 21, 741–748. https://doi.org/10.1080/14756360600810340
  14. Chohan Z.H., Youssoufi M.H., Jarrahpour A., Hadda, T.B. Eur. J. Med. Chem. 2010, 45, 1189–1199. https://doi.org/10.1016/j.ejmech.2009.11.029
  15. Beesley V.N., Peters V.J. Econ. Entomol. 1971, 64, 897–899. https://doi.org/10.1093/jee/64.4.897
  16. Beesley V.N. Ann. Trop. Med. Parasit. 1972, 66, 509–513. https://doi.org/10.1080/00034983.1972.11686854
  17. Röben C., Souto J.A., González Y., Lishchynskyi A., Muñiz K. Angew. Chem. Int. Ed. 2011, 50, 9478–9482. https://doi.org/10.1002/anie.201103077
  18. Souto J.A., Martínez C., Velilla I., Muñiz K. Angew. Chem. Int. Ed. 2013, 52, 1324–1328. https://doi.org/10.1002/anie.201206420
  19. Boursalian G.B., Ngai M.-Y., Hoijczyk K.N., Ritter T. J. Am. Chem. Soc. 2013, 135, 13278–13281. https://doi.org/10.1021/ja4064926
  20. Miao Q., Shao Z., Shi C., Ma L., Wang F., Fu R., Gao H., Li Z. Chem. Commun., 2019, 55, 7331–7334. https://doi.org/10.1039/c9cc02739d
  21. Romero R.M., Souto J.A., Muñiz K. J. Org. Chem. 2016, 81, 6118–6122. https://doi.org/10.1021/acs.joc.6b01070
  22. Sun K., Li Y., Xiong T., Zhang J., Zhang Q. J. Am. Chem. Soc. 2011, 133, 1694–1697. https://doi.org/10.1021/ja1101695
  23. Lu S., Tian L.-L., Cui T.-W., Zhu Y.-S., Zhu X., Hao X.-Q., Song M.-P., J. Org. Chem. 2018, 83, 13991–14000. https://doi.org/10.1021/acs.joc.8b02348
  24. Sun H., Han H., Yin S., Zhang S., Lin B., Cheng M., Yang L., Liu Y. Asian J. Org. Chem. 2025, 14, e202400716. https://doi.org/10.1002/ajoc.202400716
  25. Huang H., Lambert T. H. Angew. Chem. Int. Ed. 2021, 60, 11163-11167. https://doi.org/10.1002/anie.202100222
  26. Hao L., Pan Q., Zhang C., Wang S., Wang W., Zhang J., Bai L., Wang Y. Chem. Eur. J. 2021, 27, 12272-12275. https://doi.org/10.1002/chem.202102369
  27. Schroeder S., Strauch C., Gaelings N., Niggemann M. Angew. Chem. Int. Ed. 2019, 58, 5119-5123. https://doi.org/10.1002/anie.201810916
  28. Chuchmareva M., Strauch C., Schröder S., Collong A., Niggemann M., Tetrahedron Lett. 2021, 74, 153173. https://doi.org/10.1016/j.tetlet.2021.153173
  29. Gao Y., Chen S., Lu W., Gu W., Liu P., Sun P. Org. Biomol. Chem. 2017, 15, 8102-8109. https://doi.org/10.1039/C7OB02029E
  30. Yang Z., Cao K., Peng X., Lin L., Fan D., Li J.-L., Wang J., Zhang X., Jiang H., Li J. Chin. J. Chem. 2021, 39, 3347-3352. https://doi.org/10.1002/cjoc.202100489
  31. Yang L., Cao X., Xu X., Zheng H., Lai S., Chen S., Wang J., Zhu X., Wang Y., Kong X., Qiao H., Jiao M. Asian J. Org. Chem. 2025, 14, e202400718. https://doi.org/10.1002/ajoc.202400718
  32. Torti E., Protti S., Merli D., Dondi D., Fagnoni M. Chem. Eur. J. 2016, 22, 16998-17005. https://doi.org/10.1002/chem.201603522
  33. Jarboe S.G., Terrazas M.S., Beak P. J. Org. Chem. 2008, 73, 9627-9632. https://doi.org/10.1021/jo8016428
  34. Salvadori K., Chury M., Budka J., Harvalik J., Matějka P., Šimková L., Lhoták P. J. Org. Chem. 2024, 89, 1425-1437. https://doi.org/10.1021/acs.joc.3c01932
  35. Pilipenko A.S., Mel'chin V.V., Trushkov I.V., Cheshkov D.A., Butin, A.V. Tetrahedron 2012, 68, 619-627. https://doi.org/10.1016/j.tet.2011.10.114
  36. Butin A.V. Tetrahedron Lett. 2006, 47, 4113-4116. https://doi.org/10.1016/j.tetlet.2006.04.080
  37. Bartsch R.A., Allaway J.R., Yandell R.B., Lee J.G., McCann D.W. J. Chem. Eng. Data. 1977, 22, 453. https://doi.org/10.1021/je60075a025
  38. Liu N., Zhu S., Zhang X., Yin X., Dong G., Yao J., Miao Z., Zhang W., Zhang X., Sheng C. Chem. Commun. 2016, 52, 3340-3343. https://doi.org/10.1039/c5cc10594c
  39. Li D., Bao X., Pang J., Hu X., Wang L., Wang J., Yang Z., Xu L., Wang S., Weng Q., Cui S., Hou T. J. Med. Chem. 2022, 65, 15710-15724. https://doi.org/10.1021/acs.jmedchem.2c01082
  40. Beignejad H., Nematollahi D. J. Org. Chem. 2014, 79, 6326-6329. https://doi.org/10.1021/jo500812d
  41. Butin A.V., Tsiunchik F.A., Abaev V.T., Zavodnik V.E. Synlett. 2008, 8, 1145-1148. https://doi.org/10.1055/s-2008-1072720
  42. Butin A.V., Smirnov S.K., Tsiunchik F.A., Uchuskin M.G., Trushkov I.V. Synthesis. 2008, 18, 2943-2952. https://doi.org/10.1055/s-2008-1067248
  43. Nasibullina E.R., Mendogralo E.Y., Merkushev A.A., Makarov A.S., Uchuskin M.G. J. Org. Chem. 2024, 89, 6602-6606. https://doi.org/10.1021/acs.joc.4c00359
  44. Абаев В.Т., Трушков И.В., Учускин М.Г. ХГС. 2016, 52, 973-995. https://doi.org/10.1007/s10593-017-1996-x
  45. Butin A.V., Smirnov S.K., Stroganova T.A. J. Heterocycl. Chem. 2006, 43, 623-628. https://doi.org/10.1002/jhet.5570430315
  46. Mammadova G.Z., Annadurdyyeva S., Burkin G.M., Khrustalev V.N., Akkurt M., Yildirime S.Ö., Bhattarai A. Acta Crystallogr., Sect. E. 2023, E79, 499-503. https://doi.org/10.1107/S2056989023003523
  47. Mammadova G.Z., Yakovleva E.D., Burkin G.M., Khrustalev V.N., Akkurt M., Celikesir S.T., Bhattarai A. Acta Crystallogr., Sect. E. 2023, E79, 747-751. https://doi.org/10.1107/S2056989023006254
  48. Agilent. CrysAlisPRO. Agilent Technologies UK Ltd. 2013.
  49. Sheldrick G.M. Acta Crystallogr. Sect. A. 2015, 71, 3-8. https://doi.org/10.1107/S2053273314026370
  50. Sheldrick G.M. Acta Crystallogr. Sect. C. 2015, 71, 3-8. https://doi.org/10.1107/S2053229614024218

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2025 Russian Academy of Sciences

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).