Skip to main content
SpringerLink
Log in

Synthesis and properties of pyridinocalixarenes

  • Review Articles
  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

Several facets of pyridinocalixarene chemistry have been investigated including reaction pathways for their formation from the base-catalyzed alkylation of the parent calixarenes with PicCl·HCl, effect of the nature and identity of the base on regio- and stereoselectiveO-alkylations, creation of molecular asymmetry in calix[4]arenes and enantiomeric resolution, conformation and conformational mobility, and complexation.

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 and Notes

  1. C. D. Gutsche:Calixarenes. Monographs in Supramolecular Chemistry, Vol. 1, J. F. Stoddard (Ed.), The Royal Society of Chemistry, Cambridge (1989)

    Google Scholar 

  2. J. Vicens and V. Böhmer (eds.):Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht (1991).

    Google Scholar 

  3. R. Ungaro, A. Pochini, and G. D. Andreetti:J. Incl. Phenom. 2, 199 (1984).

    Google Scholar 

  4. P. J. Dijkstra, J. A. J. Brunink, K.-E. Bugge, D. N. Reinhoudt, S. Harkema, R. Ungaro, F. Ugozzoli, and E. Ghedini:J. Am. Chem. Soc. 111, 7565 (1989).

    Google Scholar 

  5. J.-D. van Loon, A. Arduini, W. Verboom, R. Ungaro, G. J. van Hummel, S. Harkema, and D. N. Reinhoudt:Tetrahedron Lett. 30, 2681 (1989).

    Google Scholar 

  6. J.-D. van Loon, A. Arduini, L. Coppi, W. Verboom, A. Pochini, R. Ungaro, S. Arkema, and D. N. Reinhoudt:J. Org. Chem. 55, 5639 (1990).

    Google Scholar 

  7. F. Bottino, L. Giunta, and S. Pappalardo:J. Org. Chem. 54, 5407 (1989).

    Google Scholar 

  8. J.-D. van Loon, D. Kraft, M. J. K. Ankoné, S. Arkema, K. Vogt, V. Böhmer, and D. N. Reinhoudt:J. Org. Chem. 55, 5176 (1990).

    Google Scholar 

  9. A. Arduini, A. Casnati, L. Dodi, A. Pochini, and R. Ungaro:J. Chem. Soc., Chem. Commun. 1597 (1990).

  10. L. C. Groenen, B. H. M. Ruel, A. Casnati, P. Timmerman, W. Verboom, S. Harkema, A. Pochini, R. Ungaro, and D. N. Reinhoudt:Tetrahedron Lett. 32, 2675 (1991).

    Google Scholar 

  11. K. A. See, F. R. Fronczek, W. H. Watson, R. P. Kashyap, and C. D. Gutsche:J. Org. Chem. 56, 7256 (1991).

    Google Scholar 

  12. K. Iwamoto, K. Araki, and S. Shinkai:Tetrahedron 47, 4325 (1991).

    Google Scholar 

  13. J. A. J. Brunink, W. Verboom, J. F. J. Engbersen, S. Harkema, and D. N. Reinhoudt:Recl. Trav. Chim. Pays-Bas 111, 511 (1992).

    Google Scholar 

  14. M. Iqbal, T. Mangiafico, and C. D. Gutsche:Tetrahedron 43, 4917 (1987).

    Google Scholar 

  15. K. Iwamoto, K. Fujimoto, T. Matsuda, and S. Shinkai:Tetrahedron Lett. 31, 7169 (1990).

    Google Scholar 

  16. C. D. Gutsche and P. A. Reddy:J. Org. Chem. 56, 4783 (1991).

    Google Scholar 

  17. K. Iwamoto, K. Araki, and S. Shinkai:J. Org. Chem. 56, 4955 (1991).

    Google Scholar 

  18. S. Pappalardo, L. Giunta, M. Foti, G. Ferguson, J. F. Gallagher, and B. Kaitner:J. Org. Chem. 57, 2611 (1992).

    Google Scholar 

  19. K. Iwamoto and S. Shinkai:J. Org. Chem. 57, 7066 (1992).

    Google Scholar 

  20. A. Casnati, P. Minari, A. Pochini, and R. Ungaro:J. Chem. Soc., Chem. Commun. 1413 (1991).

  21. J. S. Rogers and C. D. Gutsche:J. Org. Chem. 57, 3152 (1992).

    Google Scholar 

  22. S. Kanamathareddy and C. D. Gutsche:J. Org. Chem. 57, 3160 (1992).

    Google Scholar 

  23. P. Neri and S. Pappalardo:J. Org. Chem. 58, 1048 (1993).

    Google Scholar 

  24. R. G. Janssen, W. Verboom, S. Harkema, G. J. van Hummel, D. N. Reinhoudt, A. Pochini, R. Ungaro, P. Prados, and J. de Mendoza:J. Chem. Soc., Chem. Commun. 506 (1993).

  25. P. Neri, C. Geraci, and M. Piattelli:Tetrahedron Lett. 34, 3319 (1993).

    Google Scholar 

  26. S. Shinkai, T. Otsuka, K. Araki, and T. Matsuda:Bull. Chem. Soc. Jpn. 62, 4055 (1989).

    Google Scholar 

  27. P. D. Beer, J. P. Martin, and M. G. B. Drew:Tetrahedron 48, 9917 (1992).

    Google Scholar 

  28. C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No., and L. J. Bauer:Tetrahedron 39, 409 (1983).

    Google Scholar 

  29. C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto, and C. Sanchez:J. Org. Chem. 56, 3372 (1991).

    Google Scholar 

  30. G. D. Andreetti and F. Ugozzoli (Eds.):Ref. [2],. pp. 87–123.

    Google Scholar 

  31. K. Iwamoto, A. Yanagi, T. Arimura, T. Matsuda, and S. Shinkai:Chem. Lett. 1901 (1990).

  32. G. Ferguson, J. F. Gallagher, L. Giunta, P. Neri, S. Pappalardo, and M. Parisi:J. Org. Chem. 59, 42 (1994).

    Google Scholar 

  33. G. Ferguson, J. F. Gallagher, and S. Pappalardo:J. Incl. Phenom. 14, 349 (1992).

    Google Scholar 

  34. K. Iwamoto, K. Araki, and S. Shinkai:J. Chem. Soc., Perkin Trans. 1 1611 (1991).

    Google Scholar 

  35. S. Pappalardo, S. Caccamese, and L. Giunta:Tetrahedron Lett. 32, 7747 (1991).

    Google Scholar 

  36. S. Shinkai, T. Otsuka, K. Fujimoto, and T. Matsuda:Chem. Lett. 835 (1990).

  37. S. Shinkai, K. Fujimoto, T. Otsuka, and H. L. Ammon:J. Org. Chem. 57, 1516 (1992).

    Google Scholar 

  38. M. J. Schwing-Weill, F. Arnaud-Neu, and M. A. McKervey:J. Phys. Org. Chem. 5, 496 (1992).

    Google Scholar 

  39. C. D. Gutsche and K. C. Nam:J. Am. Chem. Soc. 110, 6153 (1988).

    Google Scholar 

  40. R. Muthukrishnan and C. D. Gutsche:J. Org. Chem. 44, 3962 (1979).

    Google Scholar 

  41. T. Arimura, S. Edamitsu, S. Shinkai, O. Manabe, T. Muramatsu, and M. Tashiro:Chem. Lett. 2269 (1987).

  42. S. Shinkai, T. Arimura, H. Satoh, and O. Manabe:J. Chem. Soc., Chem. Commun. 1495 (1993).

  43. K. Iwamoto, H. Shimizu, K. Araki, and S. Shinkai:J. Am. Chem. Soc. 115, 3997 (1993).

    Google Scholar 

  44. V. Böhmer, L. Merkel, and U. Kunz:J. Chem. Soc., Chem. Commun. 896 (1987).

  45. V. Böhmer, F. Marschollek, and L. Zetta:J. Org. Chem. 52, 3200 (1987).

    Google Scholar 

  46. H. Casabianca, J. Royer, A. Satrallah, A. Taty-c, and J. Vicens:Tetrahedron Lett. 28, 6595 (1987).

    Google Scholar 

  47. S. Shinkai, T. Arimura, H. Kawabata, H. Murakami, K. Araki, K. Iwamoto, and T. Matsuda.J. Chem. Soc., Chem. Commun. 1734 (1990).

  48. S. Shinkai, T. Arimura, H. Kawabata, H. Murakami, and K. Iwamoto:J. Chem. Soc., Perkin Trans. 1 2429 (1991).

    Google Scholar 

  49. L. Zetta, A. Wolff, W. Vogt, K.-L. Platt, and V. Böhmer:Tetrahedron 47, 1911 (1991).

    Google Scholar 

  50. A. Wolff, V. Böhmer, W. Vogt, F. Ugozolli, and G. D. Andreetti:J. Org. Chem. 55, 5665 (1990).

    Google Scholar 

  51. G. D. Andreetii, V. Böhmer, J. G. Gordon, M. Tabatabai, F. Ugozzoli, W. Vogt, and A. Wolff:J. Org. Chem. 58, 4023 (1993).

    Google Scholar 

  52. S. Pappalardo, L. Giunta, P. Neri, and C. Rocco:Proceedings 2nd Workshop on Calixarenes and Related Compounds, Kurume (Japan), 2–4 June 1993, OP-5.

  53. S. Caccamese and S. Pappalardo:Chirality 5, 159 (1993).

    Google Scholar 

  54. S. Pappalardo, F. Bottino, L. Giunta, M. Pietraszkiewicz, and J. Karpiuk:J. Incl. Phenom. 10, 387 (1991).

    Google Scholar 

  55. M. Pietraszkiewicz, J. Karpiuk, and A. K. Rout:Pure Appl. Chem. 65, 563 (1993).

    Google Scholar 

  56. P. Neri, M. Foti, G. Ferguson, J. F. Gallagher, B. Kaitner, M. Pons, M. A. Molins, L. Giunta, and S. Pappalardo:J. Am. Chem. Soc. 114, 7814 (1992).

    Google Scholar 

  57. P. Neri, C. Rocco, G. M. L. Consoli, and M. Piattelli:J. Org. Chem. 58, 6535 (1993).

    Google Scholar 

  58. C. D. Gutsche and L. J. Bauer:J. Am. Chem. Soc. 107, 6052 (1985).

    Google Scholar 

  59. P. D. Beer, C. A. P. Dickson, N. Fletcher, A. J. Goulden, A. Grieve, J. Hodacova, and T. Wear:J. Chem. Soc., Chem. Commun. 828 (1993).

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 8, 95125, Catania, Italy

    Francesco Bottino & Sebastiano Pappalardo

Authors
  1. Francesco Bottino
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sebastiano Pappalardo
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bottino, F., Pappalardo, S. Synthesis and properties of pyridinocalixarenes. J Incl Phenom Macrocycl Chem 19, 85–100 (1994). https://doi.org/10.1007/BF00708976

Download citation

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00708976

Key words

Search

Navigation