Skip to main content
Log in

Synthesis of imidazo[1,2-a]pyridines from α,β-unsaturated aldehydes (microreview)

  • HETEROCYCLES IN FOCUS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Methods of synthesis of imidazo[1,2-a]pyridines from α,β-unsaturated aldehydes, including α-acetylene aldehydes, and 2-aminopyridine, published during the last 10 years are reviewed in the present communication.

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. (a) Trabanco, A. A.; Tresadern, G.; Macdonald, G. J; Vega, J. A.; de Lucas, A. I.; Matesanz, E.; García, A.; Linares, M. L.; Alonso de Diego, S. A.; Alonso, J. M.; Oehlrich, D.; Ahnaou, A.; Drinkenburg, W.; Mackie, C.; Andrés, J. I.; Lavreysen, H.; Cid, J. M. J. Med. Chem. 2012, 55, 2688. (b) Stec, M. M.; Andrews, K. L.; Bo, Y.; Caenepeel, S.; Liao, H.; McCarter, J.; Mullady, E. L.; Miguel, T. S.; Subramanian, R.; Tamayo, N.; Whittington, D. A.; Wang, L.; Wu, T.; Zalameda, L. P.; Zhang, N.; Hughes, P. E.; Norman, M. H. Bioorg. Med. Chem. Lett. 2015, 25, 4136. (c) El-Sayed, W. M.; Hussin, W. A.; Al-Faiyz, Y. S.; Ismail, M. A. Eur. J. Pharmacol. 2013, 715, 212. (d) Kim, Y. B.; Kang, C. W.; Ranatunga, S.; Yang, H.; Sebti, S. M.; Del Valle, J. R. Bioorg. Med. Chem. Lett. 2014, 24, 4650. (e) E. Suloeva, E.; Yure, M.; Gudriniece, E. Chem. Heterocycl. Compd. 1999, 35, 1121. [Khim. Geterotsikl. Soedin. 1999, 1299.]

  2. (a) Bode, M. L.; Gravestock, D.; Moleele, S. S.; van der Westhuyzen, C. W.; Pelly, S. C.; Steenkamp, P. A.; Hoppe, H. C.; Khan, T.; Nkabinde, L. A. Bioorg. Med. Chem. 2011, 19, 4227. (b) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.

  3. (a) Suzuki, H.; Utsunomiya, I.; Shudo, K.; Fujimura, T.; Tsuji, M.; Kato, I.; Aoki, T.; Ino, A.; Iwaki, T. ACS Med. Chem. Lett. 2013, 4, 1074. (b) Shukla, N. M.; Salunke, D. B.; Yoo, E.; Mutz, C. A.; Balakrishna, R.; David, S. A. Bioorg. Med. Chem. 2012, 20, 5850.

  4. (a) Gladysz, R.; Adriaenssens, Y.; De Winter, H.; Joossens, J.; Lambeir, A.-M.; Augustyns, K.; Van der Veken, P. J. Med. Chem. 2015, 58, 9238. (b) Sato, Y.; Onozaki, Y.; Sugimoto, T.; Kurihara, H.; Kamijo, K.; Kadowaki, C.; Tsujino, T.; Watanabe, A.; Otsuki, S.; Mitsuya, M.; Iida, M.; Haze, K.; Machida, T.; Nakatsuru, Y.; Komatani, H.; Kotani, H.; Iwasawa, Y. Bioorg. Med. Chem. Lett. 2009, 19, 4673. (c) Baviskar, A.; Madaan, C.; Preet, R.; Mohapatra, P.; Jain, V.; Agarwal, A.; Guchhait, S. K.; Kundu, C. N.; Banerjee, U. C.; Bharatam, P. V. J. Med. Chem. 2011, 54, 5013.

  5. Ismail, M. A.; Arafa, R. K.; Wenzler, T.; Brun, R.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Bioorg. Med. Chem. 2008, 16, 683.

    Article  CAS  Google Scholar 

  6. 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  Google Scholar 

  7. Ulloora, S.; Shabaraya, R.; Aamir, S.; Adhikari, A. V. Bioorg. Med. Chem. Lett. 2013, 23, 1502.

    Article  CAS  Google Scholar 

  8. López-Martínez, M.; Salgado-Zamora, H.; Campos-Aldrete, M. E.; Trujillo-Ferrara, J. G.; Correa-Basurto, J.; Mexica-Ochoa, C. Med. Chem. Res. 2012, 21, 415.

    Article  Google Scholar 

  9. Li, L.; Li, Z.; Liu, M.; Shen, W.; Wang, B.; Guo, H.; Lu, Y. Molecules 2016, 21, 49.

    Article  Google Scholar 

  10. (a) Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Synthesis 2015, 47, 887. (b) Kumar Bagdi, A.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555.

  11. Keiko, N. A.; Vchislo, N. V.; Larina, L. I. Russ. J. Org. Chem. 2013, 49, 428. [Zh. Org. Khim. 2013, 49, 440.]

  12. Albrecht, Ł.; Albrecht, A.; Ransborg, L. K.; Jørgensen, K. A. Chem. Sci. 2011, 2, 1273.

    Article  CAS  Google Scholar 

  13. Mareev, A. V.; Medvedeva, A. S.; Mitroshina, I. V.; Afonin, A. V.; Ushakov, I. A.; Romanenko, G. V.; Tret'yakov, E. V. Russ. J. Org. Chem. 2008, 44, 1718. [Zh. Org. Khim 2008, 44, 1738.]

  14. Arnould, M.; Hiebel, M.-A.; Massip, S.; Léger, J.-M.; Jarry, C.; Berteina-Raboin, S.; Guillaumet, G. Chem.–Eur. J. 2013, 19, 12249.

  15. Tber, Z.; Hiebel, M.-A.; El Hakmaoui, A.; Akssira, M.; Guillaumet, G.; Berteina-Raboin, S. J. Org. Chem. 2015, 80, 6564.

    Article  CAS  Google Scholar 

  16. Cao, H.; Liu, X.; Zhao, L.; Cen, J.; Lin, J.; Zhu, Q.; Fu, M. Org. Lett. 2014, 16, 146.

    Article  CAS  Google Scholar 

  17. Zhan, H.; Cao, H.; Qiu, H.; Li, N.; Chen, L.; Liu, J.; Cai, H.; Tan, J. RSC Adv. 2015, 5, 32205.

    Article  CAS  Google Scholar 

  18. Zhang, H.; Jiang, L. Tetrahedron Lett. 2015, 56, 2777.

    Article  CAS  Google Scholar 

  19. Cao, H.; Liu, X.; Liao, J.; Huang, J.; Qiu, H.; Chen, Q.; Chen, Y. J. Org. Chem. 2014, 79, 11209.

    Article  CAS  Google Scholar 

  20. Zhan, H.; Zhao, L.; Liao, J.; Li, N.; Chen, Q.; Qiu, S.; Cao, H. Adv. Synth. Catal. 2015, 357, 46.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Natalia A. Keiko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(4), 222–224

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Keiko, N.A., Vchislo, N.V. Synthesis of imidazo[1,2-a]pyridines from α,β-unsaturated aldehydes (microreview). Chem Heterocycl Comp 52, 222–224 (2016). https://doi.org/10.1007/s10593-016-1867-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1867-x

Keywords

Navigation