Skip to main content
Log in

Acid-catalyzed reaction of phenols with N-(4,4-diethoxybutyl)sulfonamides – a new method for the synthesis of 2-aryl-1-sulfonylpyrrolidines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

We have developed a new method for the synthesis of 2-aryl-1-sulfonylpyrrolidines on the basis of reactions between various phenols and N-(4,4-diethoxybutyl)sulfonamides in the presence of trifluoroacetic acid. The structures of the obtained products were confirmed by 1H and 13C NMR spectroscopy, IR spectroscopy, and X-ray structural analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Figure 1
Figure 2

Similar content being viewed by others

References

  1. Noguchi, T.; Tanaka, N.; Nishimata, T.; Goto, R.; Hayakawa, M.; Sugidachi, A.; Ogawa, T.; Asai, F.; Matsui, Y.; Fujimoto, K. Chem. Pharm. Bull. 2006, 54, 163.

    Article  CAS  Google Scholar 

  2. Noguchi, T.; Tanaka, N.; Nishimata, T.; Goto, R.; Hayakawa, M.; Sugidachi, A.; Ogawa, T.; Asai, F.; Fujimoto, K. Chem. Pharm. Bull. 2007, 55, 1494.

    Article  CAS  Google Scholar 

  3. Bhattacharya, S.; Cameron, S; Dowling, M.; Fernando, D.; Ebner, D.; Filipski, K.; Kung, D.; Lee, E.; Smith, A.; Tu, M. US Patent 2003212066.

  4. Mute, V.; Vieira, E.; Wichmann, J. US Patent 6284785.

  5. Guo, T.; Gu, H.; Hobbs, D. W.; Rokosz, L. L.; Stauffer, T. M.; Jacob, B.; Clader, J. W. Bioorg. Med. Chem. Lett. 2007, 17, 3010.

    Article  CAS  Google Scholar 

  6. Cheng, X.-C.; Wang, Q.; Fang, H.; Tang, W.; Xu, W.-F. Bioorg. Med. Chem. 2 008, 16, 7932.

    Article  CAS  Google Scholar 

  7. Xu, T.; Qiu, S.; Liu, G. J. Organomet. Chem. 2011, 696, 46.

    Article  CAS  Google Scholar 

  8. Tamaru, Y.; Hojo, M.; Kawamura, S.; Yoshida, Z. J. Org. Chem. 1986, 51, 4089.

    Article  CAS  Google Scholar 

  9. Schlummer, B.; Hartwig, J. F. Org. Lett. 2 002, 4, 1471.

    Article  CAS  Google Scholar 

  10. Leger, P. R.; Murphy, R. A.; Pushkarskaya, E.; Sarpong, R. Chem.–Eur. J. 2015, 21, 4377.

  11. Yin, Y.; Zhao G. J. Fluorine Chem. 2007, 128, 40.

    Article  CAS  Google Scholar 

  12. Kresze, G.; Wagner, U. Liebigs Ann. Chem. 1972, 762, 93.

    Article  CAS  Google Scholar 

  13. Hideo, T.; Yoichiro, H.; Takahito, M.; Hiromasa, N.; Masataka, Y. J. Org. Chem. 1998, 63, 5193.

    Article  Google Scholar 

  14. O'Broin, C. Q.; Fernández, P.; Martínez, C.; Muñiz, K. Org. Lett. 2016, 18, 436.

    Article  Google Scholar 

  15. Yeom, H.-S.; So, E.; Shin, S. Chem.–Eur. J. 2011, 17, 1764.

  16. Guo, R.; Huang, J.; Huang, H.; Zhao, X. Org. Lett. 2016, 18, 504.

    Article  CAS  Google Scholar 

  17. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164.

    Article  CAS  Google Scholar 

  18. Cheng, T.; Meng, S.; Huang, Y. Org. Lett. 2013, 15, 1958.

    Article  CAS  Google Scholar 

  19. Fan, R.; Wen, F.; Qin, L.; Pu, D.; Wang, B. Tetrahedron Lett. 2007, 48, 7444.

    Article  CAS  Google Scholar 

  20. Togo, H.; Hoshina, Y.; Muraki, T.; Nakayama, H.; Yokoyama, M. J. Org. Chem. 1998, 63, 5193.

    Article  CAS  Google Scholar 

  21. Martínez, C.; Muñiz, K. Angew. Chem., Int. Ed. 2015, 54, 8287.

  22. Kamijo, S.; Amaoka, Y.; Inoue, M. Tetrahedron Lett. 2011, 52, 4654.

    Article  CAS  Google Scholar 

  23. Cernak, T. A.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 3124.

    Article  CAS  Google Scholar 

  24. Dübon, P.; Farwick, A.; Helmchen, G. Synlett. 2009, 1413.

  25. Evans, P.; McCabe, T.; Morgan, B. S.; Reau, S. Org. Lett. 2005, 7, 43.

    Article  CAS  Google Scholar 

  26. Gazizov, A. S.; Smolobochkin, A. V.; Voronina, J. K.; Burilov, A. R.; Pudovik, M. A. Synth. Commun. 2015, 45, 1215.

    Article  CAS  Google Scholar 

  27. Gazizov, A. S.; Smolobochkin, A. V.; Voronina, J. K.; Burilov, A. R.; Pudovik, M. A. Tetrahedron 2015, 71, 445.

    Article  CAS  Google Scholar 

  28. Gazizov, A. S.; Smolobochkin, A. V.; Voronina, J. K.; Burilov, A. R.; Pudovik, M. A. ARKIVOC 2014, (iv), 319.

  29. Gazizov, A. S.; Smolobochkin, A. V.; Burilov, A. R.; Pudovik, M. A. Chem. Heterocycl. Compd. 2014, 50, 707. [Khim. Geterotsikl. Soedin. 2014, 769.]

  30. Smolobochkin, A. V.; Gazizov, A. S.; Vagapova, L. I.; Burilov, A. R.; Pudovik, M. A. Russ. Chem. Bull., Int. Ed. 2014, 63, 284. [Izv. Akad. Nauk, Ser. Khim. 2014, 284.]

  31. Wei, P. H. L.; Bell, S. C.; Childress, S. J. J. Heterocycl. Chem. 1966, 3, 1.

    Article  CAS  Google Scholar 

  32. Xu, K.; Zhang, S.; Hu, Y.; Zha, Z.; Wang, Z. Chem.–Eur. J. 2013, 19, 3573.

  33. King, F. D.; Caddick, S. Org. Biomol. Chem. 2011, 9, 4361.

    Article  CAS  Google Scholar 

  34. Kamogawa, S.; Ikeda, T.; Kuriyama, M.; Matsumura, Y.; Onomura, O. Heterocycles 2010, 82, 325.

    Article  CAS  Google Scholar 

  35. Steffan, T.; Renukappa-Gutke, T.; Höfner, G.; Wanner, K. T. Bioorg. Med. Chem. 2015, 23, 1284.

    Article  CAS  Google Scholar 

  36. Aurrecoechea, J. M.; Suero, R.; de Torres, E. J. Org. Chem. 2006, 71, 8767.

    Article  CAS  Google Scholar 

  37. de Oliveira, M. C. F.; Santos, L. S.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 6995.

    Article  Google Scholar 

  38. Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.

    Article  CAS  Google Scholar 

  39. Nagasaka, T.; Tamano, H.; Maekawa, T.; Hamaguchi, F. Heterocycles 1987, 26, 617.

    Article  CAS  Google Scholar 

  40. Myers, E. L.; de Vries, J. G.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2007, 46, 1893.

  41. Camilo, N. S.; Pilli, R. A. Tetrahedron Lett. 2004, 45, 2821.

    Article  CAS  Google Scholar 

  42. de Godoy, L. A. F.; Camilo, N. S.; Pilli, R. A. Tetrahedron Lett. 2006, 47, 7853.

    Article  Google Scholar 

  43. Maki, T.; Araki, Y.; Ishida, Y.; Onomura, O.; Matsumura, Y. J. Am. Chem. Soc. 2001, 123, 3371.

    Article  CAS  Google Scholar 

  44. Klimova, V. A. Basic Micromethods for Analysis of Organic Compounds [in Russian]; Khimiya: Moscow, 1975, p. 104.

    Google Scholar 

  45. Sheldrick, G. M. SHELX-97 (Release 97-2). Programs for Crystal Structure Analysis; University of Göttingen, 1997.

  46. Spek, A. L. Acta Crystallogr., Sect. A: Found. Adv. 1 990, A46, 34.

Download references

The work was performed with financial support from the Russian Science Foundation (grant 16-13-10023).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Almir S. Gazizov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(2), 161–166

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smolobochkin, A.V., Gazizov, A.S., Anikina, E.A. et al. Acid-catalyzed reaction of phenols with N-(4,4-diethoxybutyl)sulfonamides – a new method for the synthesis of 2-aryl-1-sulfonylpyrrolidines. Chem Heterocycl Comp 53, 161–166 (2017). https://doi.org/10.1007/s10593-017-2034-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2034-8

Keywords

Navigation