Skip to main content
SpringerLink
Log in

Pyrimidino- and Proton-ionizable Pyrimidono-crown Ether Ligands: Synthesis and Preliminary Complexation Studies

Journal of inclusion phenomena and molecular recognition in chemistry volume 29, pages 301–308 (1997)Cite this article

Abstract

Pyrimidino-crown ethers were prepared in 30-50% yields by reactingthe ditosylate derivative of the appropriate oligoethylene glycol with4-methoxy-5-methyl-2,6-pyrimidinedimethanol under basic conditions. A newmacrocyclic ligand containing a proton-ionizable pyrimidone subcyclic unitwas prepared in 88% yield by treating the appropriatepyrimidino-crown ether with 5 M NaOH in 50% (v/v) aqueous methanol.Preliminary complexation properties of some of these new compounds werestudied using various NMR spectral techniques. Good enantiomeric recognitionwas exhibited by a chiral pyrimidino-crown ether for the enantiomers of1-(α-naphthyl)ethylammonium perchlorate.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

References

  1. (a)B.C. Pressman: Ann. Rev. Bioch. 45, 501–530 (1976). (b) R.W. Hay: Bio-Inorganic Chemistry Ellis Horwood: Chichester, U.K. (1984).

  2. (a)D. Dolphin, Ed. The Porphyrins Vols. I–VII, Academic Press: New York (1978). (b) R.E. Dickerson and R. Timkovich: The Enzymes Vol. XI, Boyer, P.D., Ed., Academic Press: New York (1975).

  3. C.J. Pedersen: J. Am. Chem. Soc. 89, 7017–7036 (1967).

    Google Scholar 

  4. J.J. Christensen, D.J. Eatough, and R.M. Izatt: Chem. Rev. 74, 351–384 (1974).

    Google Scholar 

  5. R.M. Izatt, J.S. Bradshaw, S.A. Nielsen, J.D. Lamb, J.J. Christensen, and D. Sen: Chem. Rev. 85, 271–339 (1985).

    Google Scholar 

  6. R.M. Izatt, K. Pawlak, J.S. Bradshaw, and R.L. Bruening: Chem. Rev. 91, 1721–2085 (1991).

    Google Scholar 

  7. R.M. Izatt, K. Pawlak, J.S. Bradshaw, and R.L. Bruening: Chem. Rev. 95, 2529–2586 (1995).

    Google Scholar 

  8. J.J. Christensen, J.O. Hill, and R.M. Izatt: Science 174, 459–467 (1971).

    Google Scholar 

  9. J.S. Bradshaw: J. Incl. Phenom. in press (1997).

  10. R.M. Izatt: J. Incl. Phenom. in press (1997).

  11. R.B. Davidson, J.S. Bradshaw, B.A. Jones, N.K. Dalley, J.J. Christensen, R.M. Izatt, F.G. Morin, and D.M. Grant: J. Org. Chem. 49, 353–357 (1984).

    Google Scholar 

  12. S.N. Vinogradov and K.H. Linnell: Hydrogen Bonding, Chapter 5. Van Nostrand Reinhold: New York (1971).

    Google Scholar 

  13. R.M. Izatt, C.-Y. Zhu, N.K. Dalley, J.C. Curtis, K.-L. Kou, and J.S. Bradshaw: J. Phys. Org. Chem. 5, 656–662 (1992).

    Google Scholar 

  14. S.P. Artz, M.P. deGradpre, and D.J. Cram: J. Org. Chem. 50, 1486–1496 (1985).

    Google Scholar 

  15. J.F. Stoddart, Topics in Stereochemistry, Vol. XVII Eliel, E.L. and Wilen, S.H., Eds., Wiley-Interscience, New York (1988).

    Google Scholar 

  16. J.S. Bradshaw, P. Huszthy, C.W. McDaniel, M. Oue, C.Y. Zhu, and R.M. Izatt: J. Coord. Chem., Section B 27, 105–114 (1992).

    Google Scholar 

  17. J.S. Bradshaw, P. Huszthy, J.T. Redd, X.X. Zhang, T. Wang, J.K. Hathaway, J.J. Young, and R.M. Izatt: Pure Appl. Chem. 67, 691–695 (1995).

    Google Scholar 

  18. J.S. Bradshaw, P. Huszthy, C.W. McDaniel, C.-Y. Zhu, N.K. Dalley, R.M. Izatt, and S. Lifson: J. Org. Chem. 55, 3129–3137 (1990).

    Google Scholar 

  19. P. Huszthy, J.S. Bradshaw, C.-Y. Zhu, R.M. Izatt, and S. Lifson: J. Org. Chem. 56, 3330–3336 (1991).

    Google Scholar 

  20. X.X. Zhang, R.M. Izatt, J.S. Bradshaw, and P. Huszthy: Anal. De Quim. Int. Ed. 92, 64–69 (1996).

    Google Scholar 

  21. C.W. McDaniel, J.S. Bradshaw, and R.M. Izatt: Heterocycles, 30, 665–706 (1990).

    Google Scholar 

  22. E. Kimura, C.A. Dalimunte, A. Yamashita, and R. Machida: J. Chem. Soc., Chem. Commun. 15, 1041–1043 (1985).

    Google Scholar 

  23. R.M. Izatt, G.C. Lindll, G.A. Clark, Y. Nakatsuji, J.S. Bradshaw, J.D. Lamb, and J.J. Christensen: J. Memb. Sci. 31, 1–13 (1987).

    Google Scholar 

  24. C.A. Chang, J. Twu, and R.A. Bartsch: Inorg. Chem. 25, 396–398 (1986).

    Google Scholar 

  25. J.T. Redd, J.S. Bradshaw, P. Huszthy, and R.M. Izatt: J. Heterocyclic Chem. 31, 1047–1052 (1994).

    Google Scholar 

  26. K.D. Cooper and H.M. Walborsky: J. Org. Chem. 46, 2110–2116 (1981).

    Google Scholar 

  27. P. Huszthy, M. Oue, J.S. Bradshaw, C.-Y. Zhu, T.-M. Wang, N.K. Dalley, J.C. Curtis, and R.M. Izatt: J. Org. Chem. 57, 5383–5394 (1992).

    Google Scholar 

  28. J.T. Redd, J.S. Bradshaw, P. Huszthy, and R.M. Izatt: unpublished observations.

  29. S.L. Baxter, and J.S. Bradshaw, J. Heterocyclic Chem. 18, 233–245 (1981).

    Google Scholar 

  30. T.-M. Wang, J.S. Bradshaw, and R.M. Izatt: J. Heterocyclic Chem. 31, 1097–1114 (1994).

    Google Scholar 

  31. M.R. Johnson, I.O. Sutherland, and R.F. Newton: J. Chem. Soc., Perkin Trans. 1 357–371 (1979).

    Google Scholar 

  32. C.-Y. Zhu: Ph.D. Dissertation, Brigham Young University, 1990.

  33. J.S. Bradshaw, D.A. Chamberlin, P.E. Harrison, B.E. Wilson, G. Arena, N.K. Dalley, J.D. Lamb, R.M. Izatt, F.G. Morin, and D.M. Grant: J. Org. Chem. 50, 3065–3069 (1985).

    Google Scholar 

  34. J.S. Bradshaw, M.L. Colter, Y. Nakatsuji, N.O. Spencer, M.F. Brown, R.M. Izatt, G. Arena, P.-K. Tse, B.E. Wilson, J.D. Lamb, N.K. Dalley, F.G. Morin, and D.M. Grant: J. Org. Chem. 50, 4865–4872 (1985).

    Google Scholar 

  35. R.M. Izatt, T. Wang, J.K. Hathaway, X.X Zhang, J.C. Curtis, J.S. Bradshaw, and C.-Y. Zhu: J. Incl. Phenom. 17, 157–175 (1994).

    Google Scholar 

  36. C.-Y. Zhu, J.S. Bradshaw, J.L. Oscarson, and R.M. Izatt: J. Incl. Phenom. 12, 275–289 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry Southern, Utah University, Cedar City, Utah, 84720, USA

    J. Ty Redd

  2. Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602-5700, USA

    Jerald S. Bradshaw & Reed M. Izatt

  3. Department of Organic Chemistry, Technical University, Budapest, Hungary

    Peter Huszthy

Authors
  1. J. Ty Redd
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jerald S. Bradshaw
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Peter Huszthy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Reed M. Izatt
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Redd, J.T., Bradshaw, J.S., Huszthy, P. et al. Pyrimidino- and Proton-ionizable Pyrimidono-crown Ether Ligands: Synthesis and Preliminary Complexation Studies. Journal of Inclusion Phenomena 29, 301–308 (1997). https://doi.org/10.1023/A:1007980102236

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1007980102236

search

Navigation