Skip to main content
Log in

Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum’s Acid

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A simple and effective method for the synthesis of substituted imidazo[1,2-a]pyridin-3-yl-acetic acids has been developed based on the multicomponent condensation of 2-aminopyridines with arylglyoxals and Meldrum's acid.

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.

Figure 1.

Similar content being viewed by others

References

  1. Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170.

    Article  CAS  PubMed  Google Scholar 

  2. Fisher, M. H.; Lusi, A. J. Med. Chem. 1972, 15, 982.

    Article  CAS  PubMed  Google Scholar 

  3. Hamdouchi, C.; Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.

    Article  CAS  PubMed  Google Scholar 

  4. Rupert, K. C.; Henry, J. R.; Dodd, J. H.; Wadsworth, S. A.; Cavender, D. E.; Olini, G. C.; Fahmy, B.; Siekierka, J. Bioorg. Med. Chem. Lett. 2003, 13, 347.

    Article  CAS  PubMed  Google Scholar 

  5. Hamdouchi, C.; Zhong, B.; Mendoza, J.; Collins, E.; Jaramillo, C.; De Diego, J. E.; Robertson, D.; Spencer, C. D.; Anderson, B. D.; Watkins, S. A.; Zhang, F.; Brooks, H. B. Bioorg. Med. Chem. Lett. 2005, 15, 1943.

    Article  CAS  PubMed  Google Scholar 

  6. Tully, W. R.; Gardner, C. R.; Gillespie, R. J.; Westwood, R. J. Med. Chem. 1991, 34, 2060.

    Article  CAS  PubMed  Google Scholar 

  7. Goodacre, S. C.; Street, L. J.; Hallett, D. M.; Crawforth, J. M.; Kelly, S.; Owens, A. P.; Blackaby, W. P.; Lewis, R. T.; Stanley, J.; Smith, A. J.; Ferris, P.; Sohal, B.; Cook, S. M.; Pike, A.; Brown, N.; Wafford, K. A.; Marshall, G.; Castro, J. L.; Atack, J. R. J. Med. Chem. 2006, 49, 35.

    Article  CAS  PubMed  Google Scholar 

  8. Lemmer, B. Physiol. Behav. 2007, 90, 285.

    Article  CAS  PubMed  Google Scholar 

  9. Kaplan, J.-P.; George, P. US Patent 4382938; Chem. Abstr. 1982, 97, 92280.

  10. Nair, D. K.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4580.

    Article  CAS  PubMed  Google Scholar 

  11. Marcinkowska, M.; Kołaczkowski, M.; Kaminski, K.; Bucki, A.; Pawłowski, M.; Siwek, A.; Karcz, T.; Mordyl, B.; Starowicz, G.; Kubowicz, P.; Pekala, E.; Wesołowska, A.; Samochowiec, J.; Mierzejewski, P.; Bienkowski, P. Eur. J. Med. Chem. 2016, 124, 456.

    Article  CAS  Google Scholar 

  12. Su, H.; Wang, L.; Rao, H.; Xu, H. Org. Lett. 2017, 19, 2226.

    Article  CAS  PubMed  Google Scholar 

  13. Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.

    Article  CAS  Google Scholar 

  14. Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.

    Article  CAS  PubMed  Google Scholar 

  15. Peshkov, V. A.; Peshkov, A. A.; Pereshivko, O. P.; Van Hecke, K.; Zamigaylo, L. L.; Van der Eycken, E. V.; Gorobets, N. Yu. ACS Comb. Sci. 2014, 16, 535.

    Article  CAS  PubMed  Google Scholar 

  16. Gorbunov, Yu. O.; Lichitsky, B. V.; Komogortsev, A. N.; Mityanov, V. S.; Dudinov, A. A.; Krayushkin, M. M. Chem. Heterocycl. Compd. 2018, 54, 692. [Khim. Geterotsikl. Soedin. 2018, 54, 692.]

  17. Wang, P.; Tao, W.-J.; Sun, X.-L.; Liao, S.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 16849.

    Article  CAS  PubMed  Google Scholar 

  18. Kutsunugi, Y.; Kawai, S.; Nakashima, T.; Kawai, T. New J. Chem. 2009, 33, 1368.

    Article  CAS  Google Scholar 

  19. Tafelska-Kaczmarek, A.; Prewysz-Kwinto, A.; Skowerski, K.; Pietrasiak, K.; Kozakiewicz, A.; Zaidlewicz, M. Tetrahedron: Asymmetry 2010, 21, 2244.

    Article  CAS  Google Scholar 

  20. Lange, J.; Karolak-Wojciechowska, J.; Wejroch, K.; Rump, S. Acta Pol. Pharm. 2001, 58, 43.

    CAS  PubMed  Google Scholar 

  21. Yang, R. F.; Li, Yu. F.; Li, Yo. Z.; Zhao, N.; Yun, L. H.; Qin, J. J.; Feng, Z. Y.; Zhang, Y. Z. EP Patent 2586780.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Andrey N. Komogortsev.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lichitsky, B.V., Tretyakov, А.D., Komogortsev, A.N. et al. Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum’s Acid. Chem Heterocycl Comp 55, 156–159 (2019). https://doi.org/10.1007/s10593-019-02432-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02432-6

Keywords

Navigation