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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. F. Aydogan and A. S. Demir, Tetrahedron, 61, 3019 (2005).

    Article  CAS  Google Scholar 

  2. A. S. Demir, A. C. Igdir, and N. B. Gunay, Tetrahedron: Asymmetry, 16, 3170 (2005).

    Article  CAS  Google Scholar 

  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. 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)].

  5. M. N. Alberti, G. C. Vougioukalakis, and M. Orfanopoulos, J. Org. Chem., 74, 7274 (2009).

    Article  CAS  Google Scholar 

  6. V. Kovtunenko, L. Potikha, and A. Turov, Synth. Commun., 34, 3609 (2004).

    Article  CAS  Google Scholar 

  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. 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. M. J. Miller, M. H. Lyttle, and A. Streitwieser, J. Org. Chem., 46, 1977 (1981).

    Article  CAS  Google Scholar 

  10. E. E. van Tamelen, and T. H. Whitesides, J. Am. Chem. Soc., 90, 3894 (1968).

    Article  Google Scholar 

  11. D. V. C. Awang and A. Vincent, J. Org. Chem., 37, 2625 (1972).

    Article  CAS  Google Scholar 

  12. W. W. Paudler and L. S. Helmick, J. Org. Chem., 33, 1087 (1968).

    Article  CAS  Google Scholar 

  13. G. Maury and C. Pigiere, Tetrahedron, 37, 91 (1981).

    Article  CAS  Google Scholar 

  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).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Taras Shevchenko Kyiv National University, 64 Volodymyrska St., Kyiv, 01033, Ukraine

    L. M. Potikha, A. R. Turelik & V. A. Kovtunenko

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  1. L. M. Potikha
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  2. A. R. Turelik
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  3. V. A. Kovtunenko
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Correspondence to L. M. Potikha.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1725-1734, November, 2011.

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Potikha, L.M., Turelik, A.R. & Kovtunenko, V.A. Synthesis of azolo[a]pyridines from 5-(bromomethyl)hept-4-en-3-one and 5-bromopent-3-en-2-one derivatives. Chem Heterocycl Comp 47, 1436–1444 (2012). https://doi.org/10.1007/s10593-012-0931-4

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  • DOI: https://doi.org/10.1007/s10593-012-0931-4

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