Advertisement

Chemistry of Heterocyclic Compounds

, Volume 47, Issue 11, pp 1436–1444 | Cite as

Synthesis of azolo[a]pyridines from 5-(bromomethyl)hept-4-en-3-one and 5-bromopent-3-en-2-one derivatives

  • L. M. PotikhaEmail author
  • A. R. Turelik
  • V. A. Kovtunenko
Article

Alkyl derivatives of 1H-imidazo[1,2-a]pyridin-4-ium, 5H-pyrido[1,2-a]benzimidazol-10-ium, 1H-[1,2,4]-triazolo[4,3-a]pyridin-4-ium, and 3-methylthiazolo[3,2-a]pyridin-4-ium bromides were obtained in two stages from (4Z)-5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one, 5-bromo-4-methylpent-3-en-2-one, or (3E)-5-bromopent-3-en-2-one by alkylation of 1-alkyl-1H-imidazoles, 1-alkyl-1H-benz-imidazoles, 1-methyl-1H-1,2,4-triazole, and 4-methylthiazole and subsequent cyclization of the quaternary azolium salts in the presence of bases.

Keywords

5-(bromomethyl)hept-4-en-3-one 5-bromopent-3-en-2-one imidazo[1,2-a]pyridine pyrido-[1,2-a]benzimidazole thiazolo[3,2-a]pyridine [1,2,4]triazolo[4,3-a]pyridine 

References

  1. 1.
    F. Aydogan and A. S. Demir, Tetrahedron, 61, 3019 (2005).CrossRefGoogle Scholar
  2. 2.
    A. S. Demir, A. C. Igdir, and N. B. Gunay, Tetrahedron: Asymmetry, 16, 3170 (2005).CrossRefGoogle Scholar
  3. 3.
    R. A. Nadzhafova, G. G. Ibragimov, R. A. Gadzhily, S. K. Zeynalova, and Kh. S. Khalilov, Azerb. Khim. Zh., № 3, 32 (2001).Google Scholar
  4. 4.
    R. A. Gadzhili, V. M. Fedoseev, N. A. Netkacheva, Ch. N. Akhmedov, and M. Sh. Sultanova, Khim. Geterotsikl. Soedin., 998 (1989). [Chem. Heterocycl. Comp., 25, 837 (1989)].Google Scholar
  5. 5.
    M. N. Alberti, G. C. Vougioukalakis, and M. Orfanopoulos, J. Org. Chem., 74, 7274 (2009).CrossRefGoogle Scholar
  6. 6.
    V. Kovtunenko, L. Potikha, and A. Turov, Synth. Commun., 34, 3609 (2004).CrossRefGoogle Scholar
  7. 7.
    L. M. Potikha, A. R. Turelik, V. A. Kovtunenko, and A. V. Turov, Khim. Geterotsikl. Soedin., 95 (2010). [Chem. Heterocycl. Comp., 46, 82 (2010)].Google Scholar
  8. 8.
    L. M. Potikha, A. R. Turelik, V. A. Kovtunenko, and A. V. Turov, Khim. Geterotsikl. Soedin., 275 (2010). [Chem. Heterocycl. Comp., 46, 223 (2010)].Google Scholar
  9. 9.
    M. J. Miller, M. H. Lyttle, and A. Streitwieser, J. Org. Chem., 46, 1977 (1981).CrossRefGoogle Scholar
  10. 10.
    E. E. van Tamelen, and T. H. Whitesides, J. Am. Chem. Soc., 90, 3894 (1968).CrossRefGoogle Scholar
  11. 11.
    D. V. C. Awang and A. Vincent, J. Org. Chem., 37, 2625 (1972).CrossRefGoogle Scholar
  12. 12.
    W. W. Paudler and L. S. Helmick, J. Org. Chem., 33, 1087 (1968).CrossRefGoogle Scholar
  13. 13.
    G. Maury and C. Pigiere, Tetrahedron, 37, 91 (1981).CrossRefGoogle Scholar
  14. 14.
    I. I. Ibragimov, E. I. Mamedov, A. T. Ismailov, A. G. Aliev, Sh. Z. Mekhtieva, V. G. Dzhafarov, and V. I. Belyaeva, Zh. Org. Khim., 26, 1648 (1990).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • L. M. Potikha
    • 1
    Email author
  • A. R. Turelik
    • 1
  • V. A. Kovtunenko
    • 1
  1. 1.Taras Shevchenko Kyiv National UniversityKyivUkraine

Personalised recommendations