Advertisement

Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 695–697 | Cite as

Open image in new window Methods of synthesis of [1,2,4]triazolo[1,5-а]pyridines (microreview)

  • Aleksey Yu. Vorob’evEmail author
Article
  • 23 Downloads

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.

Notes

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

References

  1. 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.CrossRefGoogle Scholar
  2. 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.CrossRefGoogle Scholar
  3. 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.CrossRefGoogle Scholar
  4. 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.Google Scholar
  5. 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.Google Scholar
  6. 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.Google Scholar
  7. 7.
    Bartels, B.; Bolas, C. G.; Cueni, P.; Fantasia, S.; Gaeng, N.; Trita, A. S. J. Org. Chem. 2015, 80, 1249.CrossRefGoogle Scholar
  8. 8.
    Ishimoto, K.; Nagata, T.; Murabayashi, M.; Ikemoto, T. Tetrahedron 2015, 71, 407.CrossRefGoogle Scholar
  9. 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.Google Scholar
  10. 10.
    Nettekoven, M.; Püllmann, B.; Schmitt, S. Synthesis 2003, 1649.Google Scholar
  11. 11.
    Huntsman, E.; Balsells, J. Eur. J. Org. Chem. 2005, 3761.Google Scholar
  12. 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.Google Scholar
  13. 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.]Google Scholar
  14. 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.Google Scholar
  15. 15.
    Vorob'ev, A. Y.; Supranovich, V. I.; Borodkin, G. I.; Shubin, V. G. Beilstein J. Org. Chem. 2017, 13, 800.CrossRefGoogle Scholar
  16. 16.
    Tomoike, K.; Maruoka, H.; Okabe, F.; Masumoto, E.; Fujioka, T.; Yamagata, K. Heterocycles 2014, 89, 1025.CrossRefGoogle Scholar
  17. 17.
    Alizadeh, A.; Saberi, V.; Mokhtari, J. Synlett 2013, 1825.Google Scholar
  18. 18.
    Lv, J.; He, Z.; Zhang, J.; Guo, Y.; Han, Z.; Bao, X. Tetrahedron 2018, 74, 3996.CrossRefGoogle Scholar
  19. 19.
    Zribi, L.; Zribi, F.; Marco-Contelles, J.; Chabchoub, F.; Ismaili, L. Synth. Commun. 2017, 47, 1934.CrossRefGoogle Scholar
  20. 20.
    Zhao, W.-M.; Ge, Y.-Q.; Xu, W.-R.; Zhao, G.-L.; Jia, J.; Wang, J.-W. Heterocycles 2013, 87, 869.CrossRefGoogle Scholar
  21. 21.
    Liao, Q.; Zhang, L.; Li, S.; Xi, C. Org. Lett. 2011, 13, 228.CrossRefGoogle Scholar
  22. 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.Google Scholar
  23. 23.
    Moloney, H.; Magnus, N. A.; Buser, J. Y.; Embry, M. C. J. Org. Chem. 2017, 82, 6279.CrossRefGoogle Scholar
  24. 24.
    Mammoliti, O.; Quinton, E. M.; Loones, K. T. J.; Nguyen, A. T.; Wouters, J.; Van Lommen, G. Tetrahedron 2013, 69, 1669.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

Personalised recommendations