Skip to main content
Log in

Synthesis of pyridines by cyclocondensation of acetyl and benzoyl pyruvates with enamines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

4-Ethoxycarbonylpyridines containing acetyl, benzoyl, cyclopropanoyl, and nitro groups at position 3 have been synthesized by the reaction of acetyl and benzoyl pyruvates with various enamines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. M. Stout and A. J. Meyers, Chem. Rev., 82, 223 (1982).

    Article  CAS  Google Scholar 

  2. A. E. Sausinsh and G. Ya. Duburs, Khim. Geterotsikl. Soed., 435 (1992). [Chem. Heterocycl. Comp., 28, 363 (1992).

    Google Scholar 

  3. B. E. M. Bottorff, R. G. Jones, E. C. Konfield, and M. J. Mann, J. Am. Chem. Soc., 73, 4380 (1951).

    Article  CAS  Google Scholar 

  4. G. P. Sagitullina, A. K. Garkushenko, E. G. Atavin, and R. S. Sagitullin, Mendeleev Commun., 19, 155 (2009).

    Article  CAS  Google Scholar 

  5. G. P. Sagitullina, A. K. Garkushenko, and R. S. Sagitullin, Khim. Geterotsikl. Soed., 1430 (2009). [Chem. Heterocycl. Comp., 45, 1147 (2009)].

    Google Scholar 

  6. R. Elderfield, Heterocyclic Compounds [Russian translation], Izd-vo Inosrt. Lit., Moscow, 1955, Vol. 1, p. 360.

    Google Scholar 

  7. O. Mumm and H. Huneke, Ber., 50, 1568 (1917).

    CAS  Google Scholar 

  8. O. Mumm and O. Bohme, Ber., 54, 726 (1921).

    Google Scholar 

  9. G. D. Henry, Tetrahedron, 60, 6043 (2004).

    Article  CAS  Google Scholar 

  10. C. S. Marvel and E. E. Dreger, Org. Synth. Coll., Vol. 1, 238 (1941).

    Google Scholar 

  11. C. Beyer and L. Claisen, Ber., 20, 2178 (1887).

    Google Scholar 

  12. B. J. Compton and W. C. Purdy, Can. J. Chem., 58, 2207 (1980).

    Article  CAS  Google Scholar 

  13. P. G. Baraldi, D. Simoni, and S. Manfredini, Synthesis, 902 (1983).

  14. E. Hakr, J. Kuthan, and V. Jehlička, Coll. Czechosl. Chem. Commun., 32, 4309 (1967).

    Google Scholar 

  15. C. D. Hurd and M. E. Nilson, J. Org. Chem., 20, 927 (1955).

    Article  CAS  Google Scholar 

  16. N. A. Sokolov, I. G. Tishchenko, and T. P. Kosharnaya, Vestn. Belorus. un-ta, Ser. 2, No. 2, 71 (1984): RZhKhim, 22Zh121 (1984).

  17. V. M. Lyubchanskaya, L. M. Alekseeva, and V. G. Granik, Khim. Geterotsikl. Soed., 40 (1992). [Chem. Heterocycl. Comp., 28, 34 (1992)].

    Google Scholar 

  18. G. F. Gavrilin, L. U. Bykova, T. D. Rogachkova, E. I. Novikova, and G. S. Savel'eva, Khim.-farm. Zh., 7, No. 3, 43 (1973).

    CAS  Google Scholar 

  19. T. Tokumitsu and T. Hayashi, J. Org. Chem., 50, 1547 (1985).

    Article  CAS  Google Scholar 

  20. M. A. Yurovskaya and O. D. Mit'kin, Khim. Geterotsikl. Soed., 1502 (1997). [Chem. Heterocycl. Comp., 33, 1299 (1997)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. P. Sagitullina.

Additional information

* Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1546-1550, October 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sagitullina, G.P., Garkushenko, A.K., Dushek, M.A. et al. Synthesis of pyridines by cyclocondensation of acetyl and benzoyl pyruvates with enamines. Chem Heterocycl Comp 46, 1250–1254 (2011). https://doi.org/10.1007/s10593-011-0659-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0659-6

Keywords

Navigation