Skip to main content
SpringerLink
Log in

Closure of the pyridine ring in the combes quinoline synthesis (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Closure of the pyridine ring in the Combes quinoline synthesis occurs by a type of intramolecular electrophilic substitution. With two free ortho positions the direction of ring formation depends both on the initial electrophilic attack, i.e., the nucleophilicity of the ortho carbon atom, and on the possibility of stabilizing the intermediate complex. The steric requirements of substituents both in the enaminoketone chain and in the position ortho to the point of attack exert a significant effect on the direction of ring closure. The steric factor is decisive when forming condensed angular quinoline structures.

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. R. Elderfield, Heterocyclic Compounds [Russian translation], Vol. 4 (1955), p. 7.

    Google Scholar 

  2. Z. Skraup, Ber., 13, 2086 (1880); 15, 897 (1882).

    Google Scholar 

  3. O. Döbner and W. Miller, Ber., 14, 2812 (1881).

    Google Scholar 

  4. O. Döbner and W. Miller, Ber., 16, 2464 (1883).

    Google Scholar 

  5. O. Döbner and W. Miller, Ber., 17, 1712 (1884).

    Google Scholar 

  6. A. Combes, Compt. Rend., 106, 142.

  7. A. Combes, Bull. Soc. Chim. France, 49, 89 (1888).

    Google Scholar 

  8. M. Conrad and L. Limpach, Ber., 20, 944 (1887).

    Google Scholar 

  9. M. Conrad and L. Limpach, Ber., 20, 988 (1887).

    Google Scholar 

  10. M. Conrad and L. Limpach, Ber., 24, 2990 (1891).

    Google Scholar 

  11. K. V. Vatsuro and G. D. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya Moscow (1976), p. 221.

    Google Scholar 

  12. A. N. Yakubovich and E. N. Merkulova, Zh. Obshch. Khim., 16, 55 (1946).

    Google Scholar 

  13. M. Julia, Ann. Chim. France, 5, 595 (1950).

    Google Scholar 

  14. N. K. Kochetkov, Usp. Khim., 24, 32 (1955).

    Google Scholar 

  15. J. M. F. Gagen and D. Gloyd, J. Chem. Soc. C, No. 18, 2488 (1970).

    Google Scholar 

  16. E. Roberts and E. Turner, J. Chem. Soc., 1832 (1927).

  17. C. K. Bradscher, Chem. Rev., 38, 447 (1946).

    Google Scholar 

  18. F. D. Popp and E. Mecwen, Chem. Rev., 58, 321 (1958).

    Google Scholar 

  19. T. G. Bonnder and M. Barnhard, J. Chem. Soc., No. 11, 4176 (1958).

    Google Scholar 

  20. N. P. Buu-Hoi and D. Guettier, Rec. Trav. Chim., 65, 502 (1946).

    Google Scholar 

  21. G. Saint-Ruf, J. C. Perche, and D. Asish, Bull. Soc. Chim. France, No. 7/8, 2514 (1973).

    Google Scholar 

  22. J. M. Gulland and R. Robinson, J. Chem. Soc., 1493 (1925).

  23. F. Eichler, C. S. Rooney, and H. W. R. Williams, J. Heterocycl. Chem., 13, 41 (1976).

    Google Scholar 

  24. S. Singh, R. S. Teneja, and K. S. Narang, Ind. J. Chem., No. 6, 11 (1968).

    Google Scholar 

  25. P. A. Claret and A. J. Osborne, Org. Prep. Proc., No. 4, 225 (1972).

    Google Scholar 

  26. J. V. Braun, W. Gmelin, and A. Petzold, Ber., 57, 382 (1924).

    Google Scholar 

  27. W. Markwald, Ann. Chem., 274, 331 (1893).

    Google Scholar 

  28. K. Fris, R. Walter, and K. Schilling, Ann. Chem., 516, 248 (1935).

    Google Scholar 

  29. K. Fris, Ann. Chem., 454, 121 (1927).

    Google Scholar 

  30. R. Huisgen, Ann. Chem., 559, 101 (1948).

    Google Scholar 

  31. W. S. Johnson and F. J. Mathews, J. Am. Chem. Soc., 66, 210 (1944).

    Google Scholar 

  32. J. G. Cannou, J. L. Born, and R. W. Krunnfusz, J. Heterocycl. Chem., 9, 959 (1972).

    Google Scholar 

  33. G. R. Clemo and N. Legg, J. Chem. Soc., 545 (1947).

  34. W. S. Johnson, E. Woroch, and F. J. Mathews, J. Am. Chem. Soc., 69, 566 (1947).

    Google Scholar 

  35. V. A. Petrow, J. Chem. Soc., 693 (1942).

  36. R. Huisgen, Ann. Chem., 564, 16 (1949).

    Google Scholar 

  37. F. D. Popp and P. Schujler, J. Chem. Soc., No. 1, 522 (1964).

    Google Scholar 

  38. J. L. Born, J. Org. Chem., 37, 3952 (1972).

    Google Scholar 

  39. T. G. Bonner, M. P. Thorne, and J. M. Wilkins, J. Chem. Soc., No. 7, 2358 (1955).

    Google Scholar 

  40. T. G. Bonner and M. Bernard, J. Chem. Soc., No. 7, 2351 (1955).

    Google Scholar 

  41. N. Donaldson, Chemistry and Technology of Compounds of the Naphthalene Series [Russian translation], Khim. Lit., Moscow (1963), pp. 235, 245.

    Google Scholar 

  42. J. C. Perche, G. Saint-Ruf, and N. P. Buu-Hoi, J. Chem. Soc. Perkin 1, No. 2, 260 (1972).

    Google Scholar 

  43. S. A. Yamashkin, A. N. Kost, and L. G. Yudin, Khim. Geterotsikl. Soedin., No. 10, 1428 (1976).

    Google Scholar 

  44. A. N. Kost, S. A. Yamashkin, and L. G. Yudin, Khim. Geterotsikl. Soedin., No. 6, 770 (1977).

    Google Scholar 

  45. S. A. Yamashkin, L. G. Yudin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 4, 493 (1983).

    Google Scholar 

  46. S. A. Yamashkin and N. Ya. Boriskina, Khim. Geterotsikl. Soedin., No. 2, 225 (1989).

    Google Scholar 

  47. S. A. Yamashkin, Khim. Geterotsikl. Soedin., in press.

  48. L. G. Yudin, S. A. Yamashkin, P. B. Terent'ev, and O. A. Solov'ev, Khim. Geterotsikl. Soedin., No. 10, 1381 (1979).

    Google Scholar 

  49. D. G. Yudin, A. N. Kost, E. Ya. Zinchenko, and A. G. Zhigulin, Khim. Geterotsikl. Soedin., No. 8, 1070 (1974).

    Google Scholar 

  50. F. Troxler, G. Eorbann, and F. Sceman, Helv. Chim. Acta, 51, 1214 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. E. Evsev'ev Mordov State Pedagogical Institute, 430007, Saransk

    S. A. Yamashkin, L. G. Yudin & A. N. Kost

  2. M. V. Lomonosov Moscow State University, 117234, Moscow

    S. A. Yamashkin, L. G. Yudin & A. N. Kost

Authors
  1. S. A. Yamashkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. G. Yudin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Kost
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1011–1024, August, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yamashkin, S.A., Yudin, L.G. & Kost, A.N. Closure of the pyridine ring in the combes quinoline synthesis (Review). Chem Heterocycl Compd 28, 845–855 (1992). https://doi.org/10.1007/BF00531313

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00531313

Keywords

Search

Navigation