Skip to main content
SpringerLink
Log in

Effect of copper(I) on the conformation of the thiacalixarene platform in azide-alkyne cycloaddition

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New lower-rim tetrasubstituted p-tert-butylthiacalix[4]arene derivatives bearing alkyl, propargyl, or triazole-containing substituents were synthesized. The structures of these compounds were determined by 1D and 2D NMR spectroscopy in solution and by X-ray diffraction in the solid phase. The copper-catalyzed azide-alkyne cycloaddition (CuAAC) of azides to a mixture of 1,3-alternate–partial cone stereoisomers of dipropargyl derivatives of thiacalix[4]arene affords triazole-containing products exclusively in the 1,3-alternate conformation.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Z. Asfari, V. Bohmer, J. Harrowfield, J. Vicens, Calixarenes 2001, Ed. Kluver, Netherlands, 2001.

    Google Scholar 

  2. J. Vicens, J. Harrofield, Calixarenes in Nanoworld, Springer, Netherlands, 2007.

    Book  Google Scholar 

  3. L. Mandolini, R. Ungaro, Calixarenes in Action, Imperial College Press, London, 2000.

    Book  Google Scholar 

  4. A. I. Konovalov, I. S. Antipin, Mendeleev Commun., 2008, 18, 229.

    Article  CAS  Google Scholar 

  5. R. Kumar, Y. O. Lee, V. Bhalla, M. Kumar, J. S. Kim, Chem. Soc. Rev., 2014, 43, 4824.

    Article  CAS  Google Scholar 

  6. I. Bitter, V. Csokai, Tetrahedron Lett., 2003, 44, 2261.

    Article  CAS  Google Scholar 

  7. V. Burilov, R. Nugmanov, R. Ibragimova, S. Solovieva, I. Antipin, A. Konovalov, Mendeleev Commun., 2013, 23, 113.

    Article  CAS  Google Scholar 

  8. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596.

    Article  CAS  Google Scholar 

  9. N. V. Sokolova, V. G. Nenajdenko, RSC Adv., 2013, 3, 16212.

    Article  CAS  Google Scholar 

  10. L. Liang, D. Astruc, Coord. Chem. Rev., 2011, 255, 2933.

    Article  CAS  Google Scholar 

  11. H. Matsumiya, Y. Terazono, N. Iki, S. Miyano, J. Chem. Soc., Perkin Trans. 2, 2002, 1166.

    Google Scholar 

  12. V. Csokai, A. Grün, B. Balázs, A. Simon, G. Tyth, I. Bitter, Tetrahedron, 2006, 62, 10215.

    Article  CAS  Google Scholar 

  13. A. A. Muravev, S. E. Solovieva, S. K. Latypov, I. S. Antipin, A. I. Konovalov, Phosphorus, Sulfur, Silicon Relat. Elem., 2012, 188, 499.

    Article  Google Scholar 

  14. M. Maèková, J. Mikátko, J. Budka, V. Eigner, P. Cuøínová, P. Lhoták, New J. Chem., 2015, 39, 1382.

    Article  Google Scholar 

  15. V. A. Burilov, R. I. Nugmanov, R. R. Ibragimova, S. E. Solovieva, I. S. Antipin, Mendeleev Commun., 2015, 25, 177.

    Article  CAS  Google Scholar 

  16. H. Dvorakova, J. Lang, J. Vlach, J. Sykora, M. Cyajan, M. Himl, M. Pojarova, I. Stibor, P. Lhotak, J. Org. Chem., 2007, 72, 7157.

    Article  CAS  Google Scholar 

  17. O. Kasyan, I. Thondorf, M. Bolte, V. Kalchenko, V. Boehmer, Acta Cryst., 2006, 62, 289.

    Google Scholar 

  18. S. E. Solovéva, E. V. Popova, A. O. Omran, A. T. Gubaidullin, S. V. Kharlamov, Sh. K. Latypov, I. S. Antipin, A. I. Konovalov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 486 [Izv. Akad. Nauk, Ser. Khim., 2011, 476].

    Article  Google Scholar 

  19. N. A. Epifanova, E. V. Popova, S. E. Solovieva, S. K. Latypov, I. S. Antipin, A. I. Konovalov, Macroheterocycles, 2013, 6, 47.

    Article  CAS  Google Scholar 

  20. M. Dudic, P. Lhotak, H. Petrickova, I. Stibor, K. Lang, J. Sykora, Tetrahedron, 2003, 59, 2409.

    Article  CAS  Google Scholar 

  21. V. Bhalla, M. Kumar, C. Kabuto, T. Hattori, S. Miyano, Chem. Lett., 2004, 33, 184.

    Article  CAS  Google Scholar 

  22. V. Bhalla, M. Kumar, H. Katagiri, T. Hattori, S. Miyano, Tetrahedron Lett., 2005, 46, 121.

    Article  CAS  Google Scholar 

  23. F. W. B. van Leeuwen, H. Beijleveld, H. Kooijman, A. L. Spek, W. Verboom, D. N. Reinhoudt, J. Org. Chem., 2004, 69, 3928.

    Article  Google Scholar 

  24. M. Dudic, P. Lhotak, I. Stibor, H. Petrickova, K. Lang, New J. Chem., 2004, 28, 85.

    Article  CAS  Google Scholar 

  25. L. C. Groenen, E. Steinwender, B. T. G. Lutz, J. H. van der Maas, D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1992, 1893.

    Google Scholar 

  26. X. Zeng, X. Leng, L. Chen, H. Sun, F. Xu, Q. Li, X. He, Z.-Z., J. Chem. Soc., Perkin Trans. 2, 2002, 796.

    Google Scholar 

  27. Zhan-Ting Li, Guo-Zhen Ji, Cheng-Xue Zhao, Shen-Dong Yuan, Hui Ding, Chen Huang, Ai-Lin Du, Ming Wei, J. Org. Chem., 1999, 64, 3572.

    Article  CAS  Google Scholar 

  28. V. A. Burilov, R. I. Nugmanov, E. V. Popova, I. R. Nabiullin, S. E. Soloviev, I. S. Antipin, A. I. Konovalov, Macroheterocycles, 2014, 7, 10.

    Article  Google Scholar 

  29. C. Ozen, N.Ş. Tüzün, J. Mol. Graph. Model., 2012, 34, 101.

    Article  CAS  Google Scholar 

  30. V. O. Rodionov, V. V. Fokin, Angew. Chem., Int. Ed., 2005, 44, 2210.

    Article  CAS  Google Scholar 

  31. J. E. Hein, V. V. Fokin, Chem. Soc. Rev., 2010, 39, 1302.

    Article  CAS  Google Scholar 

  32. D. Cantillo, M. Arvalos, R. Babiano, P. Cintas, J. L. Jimernez, J. C. Palacios, Org. Biomol. Chem., 2011, 9, 2952.

    Article  CAS  Google Scholar 

  33. D. N. Laikov, Y. Ustynyuk, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 820 [Izv. Akad. Nauk, Ser. Khim., 2005, 804].

    Article  CAS  Google Scholar 

  34. D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.

    Article  CAS  Google Scholar 

  35. Purification of Laboratory Chemicals, Ed. W. L. F. Armarego, C. L. L. Chai, Elsevier, New York, 2009, 743 pp.

  36. N. Iki, C. Kabuto, T. Fukushima, H. Kumagai, H. Takeya, S. Miyanari, T. Miyashi, S. Miyano, Tetrahedron, 2000, 56, 1437.

    Article  CAS  Google Scholar 

  37. J. Ritschel, F. Sasse, M. E. Maier, Eur. J. Org. Chem, 2007, 78.

    Google Scholar 

  38. S. W. Kwok, J. R. Fotsing, R. J. Fraser, V. O. Rodionov, V. V. Fokin, Org. Lett., 2010, 12, 4217.

    Article  CAS  Google Scholar 

  39. M. S. Alam, R. Kajlki, H. Hanatani, X. Kong, F. Ozoe, Y. Matsui, F. Matsumura, Y. Ozoe, J. Agric. Food Chem., 2006, 54, 1361.

    Article  CAS  Google Scholar 

  40. A. W. Gann, J. W. Amoroso, V. J. Einck, W. P. Rice, J. J. Chambers, N. A. Schnarr, Org. Lett., 2014, 16, 2003.

    Article  CAS  Google Scholar 

  41. D. Dou, G. He, Yi Li, Z. Lai, L. Wei, K. R. Alliston, G. H. Lushington, D. M. Eichhorn, W. C. Groutas, Bioorg. Med. Chem., 2010, 18, 1093.

    Article  CAS  Google Scholar 

  42. APEX2 Software Suite for Crystallographic Programs, BrukerAXS, Madison, USA, 2009.

  43. Bruker, Area Detector Control and Integration Software. Version 6.0, in SMART and SAINT, Madison, Wisconsin, Bruker Analytical X-ray Instruments Inc., 2003.

  44. G. M. Sheldrick, SADABS. Program for absorption corrections, University of Göttingen, Göttingen, Germany, 1997.

    Google Scholar 

  45. G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, 64, 112.

    Article  CAS  Google Scholar 

  46. L. J. Farrugia, J. Appl. Crystal., 1999, 32, 837.

    Article  CAS  Google Scholar 

  47. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Crystallogr., 2006, 39, 453.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Kazan (Volga region) Federal University, 18 ul. Kremlevskaya, 420088, Kazan, Russian Federation

    V. A. Burilov, R. R. Ibragimova, R. I. Nugmanov, R. R. Sitdikov, D. R. Islamov, O. N. Kataeva, S. E. Solov’eva & I. S. Antipin

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    O. N. Kataeva & S. E. Solov’eva

Authors
  1. V. A. Burilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. R. Ibragimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. I. Nugmanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. R. Sitdikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. R. Islamov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. N. Kataeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. E. Solov’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. I. S. Antipin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Burilov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2114–2124, September, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Burilov, V.A., Ibragimova, R.R., Nugmanov, R.I. et al. Effect of copper(I) on the conformation of the thiacalixarene platform in azide-alkyne cycloaddition. Russ Chem Bull 64, 2114–2124 (2015). https://doi.org/10.1007/s11172-015-1126-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1126-9

Key words

Search

Navigation