Skip to main content
Log in

Methods of synthesis of [1,2,4]triazolo[1,5-а]pyridines (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The microreview summarizes data on the synthesis of [1,2,4]triazolo[1,5-a]pyridines, published since 2002. The methods are classified according to the types of reagents used.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Menet, C. J.; Fletcher, S. R.; Van Lommen, G.; Geney, R.; Blanc, J.; Smits, K.; Jouannigot, N.; Deprez, P.; van der Aar, E. M.; Clement-Lacroix, P.; Lepescheux, L.; Galien, R.; Vayssiere, B.; Nelles, L.; Christophe, T.; Brys, R.; Uhring, M.; Ciesielski, F.; Van Rompaey, L. J. Med. Chem. 2014, 57, 9323.

    Article  CAS  PubMed  Google Scholar 

  2. Dugan, B. J.; Gingrich, D. E.; Mesaros, E. F.; Milkiewicz, K. L.; Curry, M. A.; Zulli, A. L.; Dobrzanski, P.; Serdikoff, C.; Jan, M.; Angeles, T. S.; Albom, M. S.; Mason, J. L.; Aimone, L. D.; Meyer, S. L.; Huang, Z.; Wells-Knecht, K. J.; Ator, M. A.; Ruggeri, B. A.; Dorsey, B. D. J. Med. Chem. 2012, 55, 5243.

    Article  CAS  PubMed  Google Scholar 

  3. Hamdouchi, C.; Maiti, P.; Warshawsky, A. M.; DeBaillie, A. C.; Otto, K. A.; Wilbur, K. L.; Kahl, S. D.; Patel Lewis, A.; Cardona, G. R.; Zink, R. W.; Chen, K.; Siddaramaiah, C.; Lineswala, J. P.; Neathery, G. L.; Bouaichi, C.; Diseroad, B. A.; Campbell, A. N.; Sweetana, S. A.; Adams, L. A.; Cabrera, O.; Ma, X.; Yumibe, N. P.; Montrose-Rafizadeh, C.; Chen, Y.; Reifel Miller, A. J. Med. Chem. 2017, 61, 934.

    Article  CAS  Google Scholar 

  4. (a) Song, W.; Chen, Y.; Xu, Q.; Mu, H.; Cao, J.; Huang, J.; Su, J. ACS Appl. Mater. Interfaces 2018, 10, 24689. (b) Song, W.; Gao, L.; Zhang, T.; Huang, J.; Su, J. J. Lumin. 2019, 206, 386. (c) Song, W.; Shi, L.; Gao, L.; Hu, P.; Mu, H.; Xia, Z.; Huang, J.; Su, J. ACS Appl. Mater. Interfaces 2018, 10, 5714.

  5. (а) Jones, G.; Sliskovic, D. R. Adv. Heterocycl. Chem. 1983, 83, 79. (b) Jones, G. Adv. Heterocycl. Chem. 2002, 100, 1. (c) Ibrahim, M. A.; El-Gohary, N. M. Heterocycles 2014, 89, 1125.

  6. (a) Grenda, V. J.; Jones, R. E.; Gal, G.; Sletzinger, M. J. Org. Chem. 1965, 30, 259. (b) Potts, K. T.; Burton, H. R.; Bhattacharyya, J. J. Org. Chem. 1966, 31, 260. (c) Raval, J. P.; Desai, K. R. ARKIVOC 2005, (xiii), 21. (d) Zheng, Z.; Ma, S.; Tang, L.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem. 2014, 79, 4687. (e) Song, L.; Tian, X.; Lv, Z.; Li, E.; Wu, J.; Liu, Y.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 7219.

  7. Bartels, B.; Bolas, C. G.; Cueni, P.; Fantasia, S.; Gaeng, N.; Trita, A. S. J. Org. Chem. 2015, 80, 1249.

    Article  CAS  PubMed  Google Scholar 

  8. Ishimoto, K.; Nagata, T.; Murabayashi, M.; Ikemoto, T. Tetrahedron 2015, 71, 407.

    Article  CAS  Google Scholar 

  9. (a) Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080. (b) Meng, X.; Yu, C.; Zhao, P. RSC Adv. 2014, 4, 8612.

  10. Nettekoven, M.; Püllmann, B.; Schmitt, S. Synthesis 2003, 1649.

  11. Huntsman, E.; Balsells, J. Eur. J. Org. Chem. 2005, 3761.

  12. (a) Potts, K. T.; Surapaneni, C. R. J. Heterocycl. Chem. 1970, 7, 1019.(b) Mishchuk, A.; Shtil, N.; Poberezhnyk, M.; Nazarenko, K.; Savchenko, T.; Tolmachev, A.; Krasavin, M. Tetrahedron Lett. 2016, 57, 1056.

  13. (а) Starosotnikov, A. M.; Bastrakov, M. A.; Knyazev, D. A.; Fedyanin, I. V; Kachala, V. V.; Dalinger, I. L. ChemistrySelect 2019, 4, 1510. (b) Ogoshi, Y.; Matsui, T.; Mitani, I.; Yokota, M.; Terashita, M.; Motoda, D.; Ueyama, K.; Hotta, T.; Ito, T.; Hase, Y.; Fukui, K.; Deai, K.; Yoshiuchi, H.; Ito, S.; Abeet, H. ACS Med. Chem. Lett. 2017, 8, 1320. (с) Jin, C. H.; Krishnaiah, M.; Sreenu, D.; Subrahmanyam, V. B.; Rao, K. S.; Mohan, A. V. N.; Park, C.-Y.; Son, J.-Y.; Sheen, Y. Y.; Kim, D.-K. Bioorg. Med. Chem. Lett. 2011, 21, 6049. (d) Sirakanyan, S. N.; Avetisyan, N. G.; Noravyan, A. S. Chem. Heterocycl. Compd. 2012, 48, 470. [Khim. Geterotsikl. Soedinen. 2012, 500.]

  14. (а) Tao, X.; Hu, Y. Med. Chem. 2010, 6, 65. (b) Zhang, G.; Hu, Y. J. Heterocycl. Chem. 2007, 44, 919. (c) Luo, Y.; Hu, Y. Arch. Pharm. 2006, 339, 262.

  15. Vorob'ev, A. Y.; Supranovich, V. I.; Borodkin, G. I.; Shubin, V. G. Beilstein J. Org. Chem. 2017, 13, 800.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Tomoike, K.; Maruoka, H.; Okabe, F.; Masumoto, E.; Fujioka, T.; Yamagata, K. Heterocycles 2014, 89, 1025.

    Article  CAS  Google Scholar 

  17. Alizadeh, A.; Saberi, V.; Mokhtari, J. Synlett 2013, 1825.

  18. Lv, J.; He, Z.; Zhang, J.; Guo, Y.; Han, Z.; Bao, X. Tetrahedron 2018, 74, 3996.

    Article  CAS  Google Scholar 

  19. Zribi, L.; Zribi, F.; Marco-Contelles, J.; Chabchoub, F.; Ismaili, L. Synth. Commun. 2017, 47, 1934.

    Article  CAS  Google Scholar 

  20. Zhao, W.-M.; Ge, Y.-Q.; Xu, W.-R.; Zhao, G.-L.; Jia, J.; Wang, J.-W. Heterocycles 2013, 87, 869.

    Article  CAS  Google Scholar 

  21. Liao, Q.; Zhang, L.; Li, S.; Xi, C. Org. Lett. 2011, 13, 228.

    Article  CAS  PubMed  Google Scholar 

  22. (а) Halskov, K. S.; Roth, H. S.; Ellman, J. A. Angew. Chem., Int. Ed. 2017, 56, 9183. (b) Hoang, G. L.; Ellman, J. A. Tetrahedron 2018, 74, 3318.

  23. Moloney, H.; Magnus, N. A.; Buser, J. Y.; Embry, M. C. J. Org. Chem. 2017, 82, 6279.

    Article  CAS  PubMed  Google Scholar 

  24. Mammoliti, O.; Quinton, E. M.; Loones, K. T. J.; Nguyen, A. T.; Wouters, J.; Van Lommen, G. Tetrahedron 2013, 69, 1669.

    Article  CAS  Google Scholar 

Download references

This work was supported by the Russian Science Foundation (grant 18-73-00133).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Aleksey Yu. Vorob’ev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 695–697

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vorob’ev, A.Y. Methods of synthesis of [1,2,4]triazolo[1,5-а]pyridines (microreview). Chem Heterocycl Comp 55, 695–697 (2019). https://doi.org/10.1007/s10593-019-02522-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02522-5

Navigation