Skip to main content
SpringerLink
Log in

Synthesis of 4,5-Bis(Dimethylamino)Quinolines and the Dual Direction of their Protonation

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.

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

  1. A. F. Pozharskii, V. A. Ozeryanskii, and E. A. Filatova, Khim. Geterotsikl. Soedin., 208 (2012). [Chem. Heterocycl. Compd., 48, 200 (2012)].

    Google Scholar 

  2. T. Ishikawa (editor), Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts, Wiley, Chichester (2009).

    Google Scholar 

  3. R. W. Alder, P. S. Bowman, W. R. S. Steele, and D. R. Winterman, Chem. Commun. (London), 723 (1968).

  4. A. F. Pozharskii and V. A. Ozeryanskii, in: Z. Rappoport (editor), The Chemistry of Anilines, Part 2, Wiley, Chichester (2007), p. 931.

    Chapter  Google Scholar 

  5. F. Hibbert, J. Chem. Soc., Perkin Trans. 2, 1862 (1974).

  6. R. L. Benoit, D. Lefebvre, and M. Fréchette, Can. J. Chem., 65, 996 (1987).

    Article  CAS  Google Scholar 

  7. I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Leito, and I. A. Koppel, J. Org. Chem., 70, 1019 (2005).

    Article  CAS  Google Scholar 

  8. M. A. Zirnstein and H. A. Staab, Angew. Chem., Int. Ed., 26, 460 (1987).

    Article  Google Scholar 

  9. H.-U. Wüstefeld, W. C. Kaska, F. Schüth, G. D. Stucky, X. Bu, and B. Krebs, Angew. Chem., Int. Ed., 40, 3182 (2001).

    Article  Google Scholar 

  10. R. Schwesinger, M. Mißfeldt, K. Peters, and H. G. von Schnering, Angew. Chem., Int. Ed., 26, 1165 (1987).

    Article  Google Scholar 

  11. F. B. Scriven, Chem. Soc. Rev., 12, 129 (1983).

    Article  CAS  Google Scholar 

  12. M. R. Heinrich, H. S. Klisa, H. Mayr, W. Steglich, and H. Zipse, Angew. Chem., Int. Ed., 42, 4826 (2003).

    Article  CAS  Google Scholar 

  13. A. McCurdy, L. Jimenez, D. A. Stauffer, and D. A. Dougherty, J. Am. Chem. Soc., 114, 10314 (1992).

    Article  CAS  Google Scholar 

  14. A. J. Kirby and J. M. Percy, Tetrahedron, 44, 6903 (1988).

    Article  CAS  Google Scholar 

  15. J. Verbeek, A. V. E. George, R. L. P. de Jong, and L. Brandsma, J. Chem. Soc., Chem. Commun., 257 (1984).

  16. Y. Kondo, M. Shilai, M. Uchiyama, and T. Sakamoto, J. Am. Chem. Soc., 121, 3539 (1999).

    Article  CAS  Google Scholar 

  17. B. Klei and J. H. Teuben, J. Chem. Soc., Chem. Commun., 659 (1978).

  18. F. Mongin and G. Quéguiner, Tetrahedron, 57, 4059 (2001).

    Article  CAS  Google Scholar 

  19. D. L. Comins, H. Hong, J. K. Saha, and G. Jianhua, J. Org. Chem., 59, 5120 (1994).

    Article  CAS  Google Scholar 

  20. A.-S. Rebstock, F. Mongin, F. Trécourt, and G. Quéguiner, Tetrahedron Lett., 43, 767 (2002).

    Article  CAS  Google Scholar 

  21. A. Godard, J.-M. Jacquelin, and G. Quéguiner, J. Organomet. Chem., 354, 273 (1988).

    Article  CAS  Google Scholar 

  22. Y. Tagawa, T. Kawaoka, and Y. Goto, J. Heterocycl. Chem., 34, 1677 (1997).

    Article  CAS  Google Scholar 

  23. A.-S. Rebstock, F. Mongin, F. Trécourt, and G. Quéguiner, Org. Biomol. Chem., 2, 291 (2004).

    Article  CAS  Google Scholar 

  24. C. Kaneko, A. Yamamoto, and M. Gomi, Heterocycles, 12, 227 (1979).

    Article  CAS  Google Scholar 

  25. P. D. Woodgate, J. M. Herbert, and W. A. Denny, Heterocycles, 26, 1029 (1987).

    Article  CAS  Google Scholar 

  26. J. W. Bunting and W. G. Meathrel, Can. J. Chem., 52, 951 (1974).

    Article  CAS  Google Scholar 

  27. E. Ochiai, J. Org. Chem., 18, 534 (1953).

    Article  CAS  Google Scholar 

  28. Yu. N. Bubnov, M. E. Gurskii, and T. V. Potapova, Izv. Akad. Nauk, Ser. Khim., 2807 (1996). [Russ. Chem. Bull., 45, 2665 (1996)].

  29. F. W. Vierhapper and E. L. Eliel, J. Org. Chem., 40, 2729 (1982).

    Article  Google Scholar 

  30. M. Hönel and F. W. Vierhapper, J. Chem. Soc., Perkin Trans. 1, 2607 (1982).

  31. M. Hönel and F. W. Vierhapper, Monatsh. Chem., 115, 1219 (1984).

    Article  Google Scholar 

  32. K. A. Skupinska, E. J. McEachern, R. T. Skerlj, and G. J. Bridger, J. Org. Chem., 67, 7890 (2002).

    Article  CAS  Google Scholar 

  33. B. Zacharie, N. Moreau, and C. Dockendorff, J. Org. Chem., 66, 5264 (2001).

    Article  CAS  Google Scholar 

  34. A. I. Tochilkin, I. R. Kovel’man, E. P. Prokof’ev, I. N. Gracheva, and M. V. Levinskii, Khim. Geterotsikl. Soedin., 1084 (1988). [Chem. Heterocycl. Compd., 24, 8892 (1988)].

    Google Scholar 

  35. R. H. Baker, C. J. Albisetti, R. M. Dodson, G. R. Lappin, and B. Riegel, J. Am. Chem. Soc., 68, 1532 (1946).

    Article  CAS  Google Scholar 

  36. R. W. Gouley, G. W. Moersch, and H. S. Mosher, J. Am. Chem. Soc., 69, 303 (1947).

    Article  CAS  Google Scholar 

  37. L. A. Ruchelman, J. E. Kerrigan, T.-K. Li, N. Zhou, A. Liu, L. F. Liu, and E. J. LaVoie, Bioorg. Med. Chem., 12, 3731 (2004).

    Article  CAS  Google Scholar 

  38. J. C. E. Simpson and P. H. Wright, J. Chem. Soc., 1707 (1948).

  39. A. Adams and D. H. Hey, J. Chem. Soc., 2092 (1950).

  40. W. A. Denny, G. J. Atwell, P. B. Roberta, R. F. Anderson, M. Boyd, C. J. L. Lock, and W. R. Wilson, J. Med. Chem., 35, 4832 (1992).

    Article  CAS  Google Scholar 

  41. O. V. Dyablo, E. A. Shmoilova, A. F. Pozharskii, V. A. Ozeryanskii, O. N. Burov, and Z. A. Starikova, Org. Lett., 14, 4134 (2012).

    Article  CAS  Google Scholar 

  42. A. F. Pozharskii, E. A. Zvezdina, V. I. Sokolov, and I. S. Kashparov, Chem. Ind. (Chichester, U. K.), 256 (1972).

  43. T. Birchal and W. I. Jolly, J. Am. Chem. Soc., 88, 5439 (1966).

    Article  Google Scholar 

  44. H. A. Staab, A. Kirsch, T. Barth, C. Krieger, and F. A. Neugebauer, Eur. J. Org. Chem., 1617 (2000).

  45. B. Kanner, Heterocycles, 18, 411 (1982).

    Article  CAS  Google Scholar 

  46. E. A. Filatova, I. V. Borovlev, A. F. Pozharskii, Z. A. Starikova, and N. V. Vistorobskii, Mendeleev Commun., 10, 178 (2000).

    Article  Google Scholar 

  47. F. Hibbert, Acc. Chem. Res., 17, 115 (1984).

    Article  CAS  Google Scholar 

  48. V. A. Ozeryanskii, A. F. Pozharskii, A. Filarowski, and G. S. Borodkin, Org. Lett., 15, 2194 (2013).

    Article  CAS  Google Scholar 

  49. J. Azizian, H. Kefayati, M. Mehrdad, K. Jadidi, and Y. Sarrafi, Iran J. Chem. Chem. Eng., 20, 20 (2001).

    CAS  Google Scholar 

  50. R. W. Gouley, G. W. Moersch, and H. S. Mosher, J. Am. Chem. Soc., 69, 303 (1947).

    Article  CAS  Google Scholar 

  51. M. Karramkam, F. Dolle, H. Valette, L. Besret, Y. Bramoulle, F. Hinnen, F. Vaufrey, C. Franklin, S. Bourg, C. Coulon, M. Ottaviani, M. Delaforge, C. Loch, M. Bottlaender, and C. Crouzela, Bioorg. Med. Chem., 10, 2611 (2002).

    Article  CAS  Google Scholar 

  52. E. Ochiai and T. Okamoto, J. Pharm. Soc. Jpn, 68, 88 (1948); Chem. Abstr., 47, 8073 (1953).

    Google Scholar 

Download references

This work was carried out with the financial support of the Russian Foundation for Basic Research (grant 11-03-00073).

Author information

Authors and Affiliations

  1. Southern Federal University, 7 Zorge St., Rostov-on-the-Don, 344090, Russia

    E. A. Shmoilova, O. V. Dyablo & A. F. Pozharskii

Authors
  1. E. A. Shmoilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Dyablo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. F. Pozharskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. V. Dyablo.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1404-1419, September, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shmoilova, E.A., Dyablo, O.V. & Pozharskii, A.F. Synthesis of 4,5-Bis(Dimethylamino)Quinolines and the Dual Direction of their Protonation. Chem Heterocycl Comp 49, 1308–1322 (2013). https://doi.org/10.1007/s10593-013-1380-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1380-4

Keywords

Search

Navigation