Skip to main content
Log in

Methodology of C(sp2)—H functionalization in mono- and diazine N-oxides in the synthesis of heterocyclic meso-substituted calixarenes

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

Abstract

Earlier unknown meso-substituted azinylcalixarenes were obtained by a direct cross-coupling of 2-lithium-25,26,27,28-tetramethoxycalix[4]arenes with mono- and diazine N-oxides without transition metal catalysis.

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.

Similar content being viewed by others

References

  1. Cross Coupling and Heck-Type Reactions 03: Metal-Catalyzed Heck-Type Reactions and C—C Cross Coupling via C—H Activation, Ed. M. Larhed, Thieme Medical Publishers, Stuttgart, 2013, 892 pp.

    Google Scholar 

  2. J. J. Mousseau, B. A. B. Charette, Acc. Chem. Res., 2013, 46, 412.

    Article  CAS  Google Scholar 

  3. S. I. Kozhushkov, H. K. Potukuchi, L. Ackermann, Catal. Sci. Technol., 2013, 3, 562.

    Article  CAS  Google Scholar 

  4. R. A. Sheldon, Pure Appl. Chem., 2000, 72, 1233.

    Article  CAS  Google Scholar 

  5. B. M. Trost, Science, 1991, 254, 1471.

    Article  CAS  Google Scholar 

  6. Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Negishi, A. de Meijere, John Wiley & Sons, New York, 2002, Vol. 1, 2, 3424 pp.

    Google Scholar 

  7. A. de Meijere, F. Diederich, Metal-catalyzed Cross-coupling Reactions, 2nd ed., John Wiley & Sons, Weinheim, 2004, 540 pp.

    Book  Google Scholar 

  8. J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon Press, Oxford, 2000, 658 pp.

    Google Scholar 

  9. Metal Free C—H Functionalization of Aromatics Nucleophilic Displacement of Hydrogen, Eds V. Charushin, O. Chupakhin

  10. In Topics in Heterocyclic Chemistry, Eds B. U. W. Maes, J. Cossy, S. Polanc, Springer, Switzerland, 2014, Vol. 37, 283 pp.

  11. O. N. Chupakhin, V. N. Charushin, H. C. van der Plas, Nucleophilic aromatic substitution of hydrogen, Academic Press, New York, San Diego, 1994, 367 pp.

    Google Scholar 

  12. F. Terrier, Modern Nucleophilic Aromatic Substitution, WileyVCH, Weinheim, 2013, 488 pp.

    Book  Google Scholar 

  13. M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin, Makrogeterotsikly [Macroheterocycles], 2013, 6, 308 (in Russian).

    CAS  Google Scholar 

  14. J. W. Steed, J. L. Atwood, Supramolecular Chemistry, 2nd ed., John Wiley & Sons, Chichester, 2009, 1002 pp.

    Book  Google Scholar 

  15. M. Deska, B. Dondela, W. Sliwa, Arkivoc, 2015, (i), 29.

    Google Scholar 

  16. W. Sliwa, M. Deska, Arkivoc, 2012, (i), 173.

    Google Scholar 

  17. K. S. J. Iqbal, P. J. Cragg, Dalton Trans., 2007, 26.

    Google Scholar 

  18. O. A. Okunola, J. L. Seganish, K. J. Salimian, P. Y. Zavalij, J. T. Davis, Tetrahedron, 2007, 63, 10743.

    Article  CAS  Google Scholar 

  19. V. I. Kalchenko, Pure Appl. Chem., 2008, 80, 1449.

    Article  CAS  Google Scholar 

  20. G. Hennrich, M. T. Murillo, P. Prados, K. Song, I. Asselberghs, K. Clays, A. Persoons, J. Benet-Buchholzc, J. de Mendozac, Chem. Commun., 2005, 2747.

    Google Scholar 

  21. J. B. Simoes, D. L. da Silva, A. de Fatima, S. A. Fernandes, Curr. Org. Chem., 2012, 16, 949.

    Article  CAS  Google Scholar 

  22. S. Andr, F. Sansone, H. Kaltner, A. Casnati, J. Kopitz, H.-J. Gabius, R. Ungaro ChemBioChem., 2008, 9, 1649.

    Article  Google Scholar 

  23. P. A. Scully, T. M. Hamilton, J. L. Bennett, Org. Lett., 2001, 3, 2741.

    Article  CAS  Google Scholar 

  24. C. Fischer, W. Seichter, E. Weber, Beilstein J. Org. Chem., 2011, 7, 1602.

    Article  CAS  Google Scholar 

  25. C. Fischer, M. Stapf, W. Seichter, E. Weber, Supramol. Chem., 2013, 25, 371.

    Article  CAS  Google Scholar 

  26. C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No, L. J. Bauer, Tetrahedron, 1983, 39, 409.

    Article  CAS  Google Scholar 

  27. H. Yamanaka, H. Sakamoto, H. Niitsuma, Heterocycles, 1990, 31, 923.

    Article  CAS  Google Scholar 

  28. F. W. J. Demnitz, M. B. D′Heni, Org. Prep. Proced. Int., 1998, 30, 467.

    Article  CAS  Google Scholar 

  29. J. F. J. Engbersen, A. Koudijs, M. H. A. Joosten, H. C. Vanderplas, J. Heterocycl. Chem., 1986, 23, 989.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. N. Chupakhin.

Additional information

On the occasion of the 100th anniversary of the birth of Academician N. K. Kochetkov (1915—2005).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1093—1096, May, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Varaksin, M.V., Chupakhin, O.N., Charushin, V.N. et al. Methodology of C(sp2)—H functionalization in mono- and diazine N-oxides in the synthesis of heterocyclic meso-substituted calixarenes. Russ Chem Bull 64, 1093–1096 (2015). https://doi.org/10.1007/s11172-015-0984-5

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0984-5

Keywords

Navigation