Skip to main content
SpringerLink
Log in

Transformations of Substituted Oxazolo- [3,2-a]Pyridines to 5,6-Disubstituted Indolizines: Synthesis And X-ray Structural Mapping

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The treatment of 4,6-dimethyl-2-oxonicotinic nitrile, amide, and ethyl ester with p-bromophenacyl bromide produced N-alkyl isomers, which cyclized in the presence of mineral acids to the oxazolo-[3,2-a]pyridinium cations without changes in the functional groups. The obtained compounds underwent recyclization to 6-Х-5-aminoindolizines (X = CN, CONH2, CO2Et) upon treatment with morpholine. The compounds were characterized by X-ray structural analysis.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Е. V. Babaev and A. V. Efimov, Khim. Geterotsikl. Soedin., 998 (1997). [Chem. Heterocycl. Compd., 33, 875 (1997).]

    Article  CAS  Google Scholar 

  2. E. V. Babaev, A. V. Efimov, D. A. Maiboroda, and K. Jug, Eur. J. Org. Chem., 193 (1998).

  3. E. V. Babaev, А. V. Efimov, S. G. Zhukov, and V. B. Rybakov, Khim. Geterotsikl. Soedin., 983 (1998). [Chem. Heterocycl. Compd., 34, 852 (1998).]

    Article  CAS  Google Scholar 

  4. E. V. Babaev, J. Heterocycl. Chem., 37, 519 (2000).

    Article  CAS  Google Scholar 

  5. E. V. Babaev and V. L. Alifanov, Izv. Akad. Nauk, Ser. Khim., 8, 1675 (2007).

    Google Scholar 

  6. E. V. Babaev, V. L. Alifanov, and А. V. Efimov, Izv. Akad. Nauk, Ser. Khim., 4, 837 (2008).

    Google Scholar 

  7. E. V. Babaev, Khim. Geterotsikl. Soedin., 64 (2012). [Chem. Heterocycl. Compd., 48, 59 (2012).]

    Article  CAS  Google Scholar 

  8. P. Tielmann and C. Hoenke, Tetrahedron Lett., 47, 261 (2006).

    Article  CAS  Google Scholar 

  9. V. B. Rybakov, A. A. Bush, E. V. Babaev, and L. A. Aslanov, Acta Crystallogr., Sect. E: Struct. Rep. Online, E60, o160 (2004).

    Article  Google Scholar 

  10. B. J. Witkop, J. Am. Chem. Soc., 70, 3712 (1948).

    Article  CAS  Google Scholar 

  11. G. G. Danagulyan and L. G. Saakyan, Khim. Geterotsikl. Soedin., 395 (2004). [Chem. Heterocycl. Compd., 40, 320 (2004).]

    Article  CAS  Google Scholar 

  12. G. G. Danagulyan, L. G. Saakyan, A. R. Katritzky, and S. N. Denisenko, Khim. Geterotsikl. Soedin., 1572 (1999). [Chem. Heterocycl. Compd., 35, 1375 (1999).]

    Article  CAS  Google Scholar 

  13. D. V. Albov, O. S. Mazina, V. B. Rybakov, E. V. Babaev, and V. V. Chernyshev, Kristallografiya, 49, 208 (2004).

    Google Scholar 

  14. D. V. Albov, E. I. Turubanova, V. B. Rybakov, E. V. Babaev, and L. A. Aslanov, Acta Crystallogr., Sect. E: Struct. Rep. Online, E60, o1222 (2004).

    Article  Google Scholar 

  15. K. Gevald and H. J. Jansch, J. Prakt. Chem., 318, 313 (1976).

    Article  Google Scholar 

  16. C. F. Lin, Y. F. Lin, Y. C. Lo, K. T. Chen, and T. L. Su, Heterocycles, 53, 15 (2000).

    Article  CAS  Google Scholar 

  17. E. V. Babaev, N. I. Vasilevich, and A. S. Ivushkina, Beilstein J. Org. Chem., 1, No. 9 (2005), doi:10.1186/1860-5397-1-9.

  18. C. K. Bradsher and M. F. Zinn, J. Heterocycl. Chem., 1, 219 (1964).

    Article  CAS  Google Scholar 

  19. D. V. Albov, E. I. Turubanova, V. B. Rybakov, E. V. Babaev, and L. A. Aslanov, Acta Crystallogr., Sect. E: Struct. Rep. Online, E60, o1303 (2004).

    Article  Google Scholar 

  20. L. J. Farrugia, J. Appl. Crystallogr., 32, 837 (1999).

    Article  CAS  Google Scholar 

  21. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Article  Google Scholar 

  22. L. J. Farrugia, J. Appl. Crystallogr., 30, 565 (1997).

    Article  CAS  Google Scholar 

Download references

This project received financial support from the Russian Foundation for Basic Research (grant 12-03-00644-а).

The authors would like to express their gratitude to Е. I. Turubanova and А. V. Efimov for their assistance.

Author information

Authors and Affiliations

  1. Moscow M. V. Lomonosov State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    V. B. Rybakov & E. V. Babaev

Authors
  1. V. B. Rybakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Babaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Babaev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 250-261, February, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rybakov, V.B., Babaev, E.V. Transformations of Substituted Oxazolo- [3,2-a]Pyridines to 5,6-Disubstituted Indolizines: Synthesis And X-ray Structural Mapping. Chem Heterocycl Comp 50, 225–236 (2014). https://doi.org/10.1007/s10593-014-1465-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1465-8

Keywords

Search

Navigation