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Effect of the solvent nature on the course of quaternization of 3,5-diethoxycarbonyl-2,6-dimethyl-4-(3-pyridyl)-1,4-dihydropyridine

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Chemistry of Heterocyclic Compounds Aims and scope

The effect of the solvent nature and temperature on the quaternization of 3,5-diethoxycarbonyl-2,6-di- methyl-4-(3-pyridyl)-1,4-dihydropyridine by lipophilic alkyl bromides has been investigated. By comparison of the solvent effect (acetone, acetonitrile, and 2-butanone) on the alkylation of the pyridine fragment of 3,5-diethoxycarbonyl-2,6-dimethyl-4-(3-pyridyl)-1,4-dihydropyridine it was established that conducting the reaction in acetonitrile at 81 °C is the most optimal.

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References

  1. K. Fujimoto, D. Morisaki, M. Yoshida, T. Namba, K. Hye-Sook, Y. Wataya, H. Kourai, H. Kakuta, andK. Sasaki, Bioorg. Med. Chem. Lett., 16, 2758 (2006).

    Article  CAS  Google Scholar 

  2. M. A. Ilies, W. A. Seitz, B. H. Johnson, E. L. Ezell, A. L. Miller, E. B. Thompson, and A. T. Balaban, J. Med. Chem., 49, 3872 (2006).

    Article  CAS  Google Scholar 

  3. A. Riahi, M. Wurster, M. Lalk, U. Lindequist, and P. Langer, Bioorg. Med. Chem., 17, 4323 (2009).

    Article  CAS  Google Scholar 

  4. V. Onnis, M. T. Cocco, R. Fadda, and C. Congiu, Bioorg. Med. Chem., 17, 6158 (2009).

    Article  CAS  Google Scholar 

  5. B. Vroman, M. Mazza, M. R. Fernandez, R. Jerome, and V. Preat, J. Controlled Release, 118, 136 (2007).

    Article  CAS  Google Scholar 

  6. A. Mishra, N. K. Kaushik, A. K. Verma, and R. Gupta, Eur. J. Med. Chem., 43, 2189 (2008).

    Article  CAS  Google Scholar 

  7. Z. Dega-Szafran, G. Schroeder, and M. Szafran, J. Phys. Org. Chem., 12, 39 (1999).

    Article  CAS  Google Scholar 

  8. N. V. Makarova, A. Plotniece, G. Tirzitis, I. Turovskii, and G. Dubur, Khim. Geterotsikl. Soedin., 202 (1997). [Chem. Heterocycl. Comp., 33, 175 (1997)].

    Google Scholar 

  9. S.-H. Zhao, H.-R. Zhang, L.-H. Feng, and Z.-B. Chen, J. Mol. Catal. A: Chem., 258, 251 (2006).

    Article  CAS  Google Scholar 

  10. S. Kumar and S. K. Pal, Tetrahedron Lett., 46, 4127 (2005).

    Article  CAS  Google Scholar 

  11. A. A. P. Meekel, A. Wagenaar, J. Smisterova, J. E. Kroeze, P. Haadsma, B. Bosgraaf, M. C. A. Stuart, A. Brisson, M. H. J. Ruiters, D. Hoekstra, and J. B. F. N. Engberts, Eur. J. Org. Chem., 665 (2000).

  12. A. Roosjen, J. Smisterova, C. Driessen, J. T. Anders, A. Wagenaar, D. Hoekstra, R. Hulst, andJ. B. F. N. Engberts, Eur. J. Org. Chem., 1271 (2002).

  13. D. Pijper, E. Bulten, J. Smisterova, A. Wagenaar, D. Hoekstra, J. B. F. N. Engberts, and R. Hulst, Eur. J. Org. Chem., 4406 (2003).

  14. M. A. Ilies, W. A. Seitz, I. Ghiviriga, B. H. Johnson, A. Miller, E. B. Thompson, and A. T. Balaban,J. Med. Chem., 47, 3744 (2004).

    Article  CAS  Google Scholar 

  15. T. H. Kim, K. Kuca, D. Jun, and Y. S. Jung, Bioorg. Med. Chem. Lett., 15, 2914 (2005).

    Article  CAS  Google Scholar 

  16. C. M. Timperley, M. Bird, S. C. Heard, S. Notman, R. W. Read, J. E. H. Tattersall, and S. R. Turner, J. Fluorine Chem., 126, 1160 (2005).

    Article  CAS  Google Scholar 

  17. K. Wojciechowski and S. Kosinski, Tetrahedron, 57, 5009 (2001).

    Article  CAS  Google Scholar 

  18. J. Pernak, J. Kalewska, H. Ksycinska, and J. Cybulski, Eur. J. Med. Chem., 36, 899 (2001).

    Article  CAS  Google Scholar 

  19. R. Hulst, J. Muizebelt, P. Oosting, C. van der Pol, A. Wagenaar, J. Smisterova, E. Bulten, C. Driessen, D. Hoekstra, and J. B. F. N. Engberts, Eur. J. Org. Chem., 835 (2004).

  20. L. Dagnino, M. C. Li-Kwong-Ken, M. W. Wolowyk, C. R. Triggle, and E. E. Knaus, Eur. J. Med. Chem., 22, 499 (1987).

    Article  CAS  Google Scholar 

  21. G. D. Tirzit, N. V. Makarova, and G. Ya. Dubur, Izv. Akad. Nauk LatvSSR, Ser. Khim., 369 (1990).

  22. N. V. Makarova, Zh. V. Koronova, A. V. Plotniece, D. Ya. Tirzite, G. D. Tirzit, and G. Ya. Duburs, Khim. Geterotsikl. Soedin., 1112 (1995). [Chem. Heterocycl. Comp., 31, 969 (1995)].

  23. J. Joule and G. Smith, Fundamentals of the Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow (1975).

    Google Scholar 

  24. http://macro.lsu.edu/howto/solvents/Polarity%20index.htm.

  25. S. Shaik, A. Ioffe, A. C. Reddy, and A. Pross, J. Am. Chem. Soc., 116, 262 (1994).

    Article  CAS  Google Scholar 

  26. W. Brand-Williams, M. E. Cuvelier, and C. Berset, Lebensm.-Wiss. Technol., 28, 25 (1995).

    Article  CAS  Google Scholar 

  27. D. Ya. Tirzite, Zh. V. Khyuvonen, A. G. Shmidlers, G. D. Tirzitis, and G. Ya. Duburs, Pharm. Chem. J., 34, 297 (2000).

    Article  CAS  Google Scholar 

  28. R. H. Wiley and J. S. Ridgway, J. Org. Chem., 26, 595 (1961).

    Article  CAS  Google Scholar 

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Correspondence to A. Plotniece.

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Dedicated to Academician Valery Nikolaevich Charushin on his jubilee.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 721–726, May, 2011.

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Pajuste, K., Gosteva, M., Kaldre, D. et al. Effect of the solvent nature on the course of quaternization of 3,5-diethoxycarbonyl-2,6-dimethyl-4-(3-pyridyl)-1,4-dihydropyridine. Chem Heterocycl Comp 47, 597–601 (2011). https://doi.org/10.1007/s10593-011-0803-3

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  • DOI: https://doi.org/10.1007/s10593-011-0803-3

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