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

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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.

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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 

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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

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  1. J. Ty Redd
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  2. Jerald S. Bradshaw
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  3. Peter Huszthy
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  4. Reed M. Izatt
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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

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