Advertisement

Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 167–172 | Cite as

Synthesis of 1,2,3-triazoles linked into chains with other carbo- and heterocycles by a reaction between β-azolyl enamines and azides

  • Ilya V. Efimov
  • Nikolai A. Beliaev
  • Vasiliy A. Bakulev
  • Tetyana V. Beryozkina
Article
  • 82 Downloads

The reactions of β-azolyl enamines with azides proceeded under solvent-free conditions in the absence of base at 110°С by one of the possible routes, selectively forming 1,4-disubstituted 1,2,3-triazoles. The proposed reaction mechanism includes cycloaddition of the starting reagents, leading to 1,2,3-triazoline intermediates, followed by elimination of dimethylamine and the formation of aromatic triazole ring.

Keywords

azides enamines linear chains of ring systems 1,2,3-triazoles triazolines 

Notes

This work received financial support from the Russian Science Foundation (grant 15-13-10031).

References

  1. 1.
    De Carvalho da Silva, F.; Cardoso, M. F. C.; Ferreira, P. G.; Ferreira, V. F. Top. Heterocycl. Chem. 2015, 40, 117.Google Scholar
  2. 2.
    Leban, J.; Baumgartner, R.; Saeb, W.; Chevrier, C. WO Patent 2012101261.Google Scholar
  3. 3.
    Li, W.-T.; Wu, W.-H.; Tang, C.-H.; Tai, R.; Chen, S.-T. ACS Comb. Sci. 2011, 13, 72.CrossRefGoogle Scholar
  4. 4.
    Olesen, P. H.; Sørensen, A. R.; Ursø, B.; Kurtzhals, P.; Bowler, A. N.; Ehrbar, U.; Hansen, B. F. J. Med. Chem. 2003, 46, 3333.CrossRefGoogle Scholar
  5. 5.
    Lu, R. J.; Pickens, J. C.; Tucker, J. A.; Zinevitch, T.; Sviridov, S.; Konoplev, V. WO Patent 2007103456.Google Scholar
  6. 6.
    Leclerc, J.-P.; Li, C. S.; Ramtohul, Y. K. WO Patent 2010025553.Google Scholar
  7. 7.
    Hirose, T.; Sunazuka, T.; Noguchi, Y.; Yamaguchi, Y.; Hanaki, H.; Sharpless, K. B.; Omura, S. Heterocycles 2006, 69, 55.CrossRefGoogle Scholar
  8. 8.
    Sapountzis, I.; Ettmayer, P.; Klein, C.; Mantoulidis, A.; Steegmaier, M.; Steurer, S.; Waizenegger, I. WO Patent 2009003998.Google Scholar
  9. 9.
    Patil, P.; Madhavachary, R.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Dömling, A. Org. Lett. 2017, 19, 642.CrossRefGoogle Scholar
  10. 10.
    Sinn, S.; Biedermann, F.; De Cola, L. Chem.–Eur. J. 2017, 23, 1965.CrossRefGoogle Scholar
  11. 11.
    Kaur, T.; Gautam, R. N.; Sharma, A. Chem.–Asian J. 2016, 11, 2938.CrossRefGoogle Scholar
  12. 12.
    Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389.CrossRefGoogle Scholar
  13. 13.
    Watkinson, M. Top. Heterocycl. Chem. 2012, 28, 109.Google Scholar
  14. 14.
    Potratz, S.; Mishra, A.; Bäuerle, P. Beilstein J. Org. Chem. 2012, 8, 683.Google Scholar
  15. 15.
    van Steenis, D. J. V. C.; David, O. R. P.; van Strijdonck, G. P. F.; van Maarseveen, J. H.; Reek, J. N. H. Chem. Commun. 2005, 4333.Google Scholar
  16. 16.
    Kulhánek, J.; Ludwig, M.; Bureš, F.; Tydlitát, J. Chem. Heterocycl. Compd. 2017, 53, 46. [Khim. Geterotsikl. Soedin. 2017, 53, 46.]Google Scholar
  17. 17.
    Kostyuchenko, A. S.; Drozdova, E. A.; Fisyuk, A. S. Chem. Heterocycl. Compd. 2017, 53, 92. [Khim. Geterotsikl. Soedin. 2017, 53, 92.]Google Scholar
  18. 18.
    Horčic, M.; Kozmík, V.; Svoboda, J.; Novotná, V.; Pociecha, D. J. Mater. Chem. C 2013, 1, 7560.CrossRefGoogle Scholar
  19. 19.
    Kim, M.-H.; Nam, Y.-K.; Choi, E.-J. J. Inf. Disp. 2017, 18, 31.CrossRefGoogle Scholar
  20. 20.
    Tornøe, C. W.; Chistensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.CrossRefGoogle Scholar
  21. 21.
    Rostovtsev, V. V.; Green, L. G., Fokin V. V.; Sharpless, B. K. Angew. Chem., Int. Ed. 2002, 41, 2596.Google Scholar
  22. 22.
    Crowley, J. D.; McMorran, D. A. Top Heterocycl. Chem. 2012, 28, 31.Google Scholar
  23. 23.
    Lee, S.; Flood, A. H. Top Heterocycl. Chem. 2012, 28, 85.Google Scholar
  24. 24.
    Zheng, T.; Rouhanifard, S. H.; Jalloh, A. S.; Wu, P. Top Heterocycl. Chem. 2012, 28, 163.Google Scholar
  25. 25.
    Bakulev, V. A.; Dehaen, W. The Chemistry of 1,2,3-Thiadiazoles; John Wiley & Sons Inc.: Hoboken, Heidelberg, New York, Dordrecht, London, 2004, 241 pp.CrossRefGoogle Scholar
  26. 26.
    Mignani, S.; Zhou, Y.; Lecourt, T.; Micouin, L. Top Heterocycl. Chem. 2012, 28, 185.Google Scholar
  27. 27.
    Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339. [Usp. Khim. 2005, 74, 369.]Google Scholar
  28. 28.
    Bakulev, V. A.; Morzherin, Yu. Yu.; Lebedev, A. T.; Dankova, E. F.; Kolobov, M. Yu.; Shafran, Yu. M. Bull. Soc. Chim. Belg. 1993, 102, 493.CrossRefGoogle Scholar
  29. 29.
    Bakulev, V. A. Rus. Chem. Rev. 1995, 64, 99. [Usp. Khim. 1995, 64, 107.]Google Scholar
  30. 30.
    Shafran, Yu. M.; Bakulev, V. A.; Mokrushin, V. S.; Alexeev, S. G. Chem. Heterocycl. Compd. 1984, 20, 1038. [Khim. Geterotsikl. Soedin. 1984, 1266.]Google Scholar
  31. 31.
    Bakulev, V. A.; Chiang, Y.; Kresge, A. J.; Meng, Q.; Morzherin, Y. Y.; Popik, V. V. J. Am. Chem. Soc. 2001, 123, 2681.CrossRefGoogle Scholar
  32. 32.
    Bakulev, V. A.; Beryozkina, T. V. Chem. Heterocycl. Compd. 2016, 52, 4. [Khim. Geterotsikl. Soedin. 2016, 52, 4.]Google Scholar
  33. 33.
    Bakulev, V. A.; Efimov, I. V.; Belyaev, N. A.; Rozin, Yu. A.; Volkova, N. N.; El'tsov, O. S. Chem. Heterocycl. Compd. 2012, 47, 1593. [Khim. Geterotsikl. Soedin. 2011, 1900.]Google Scholar
  34. 34.
    Bakulev, V. A.; Efimov, I. V.; Belyaev, N. A.; Zhidovinov, S. S.; Rozin, Yu. A.; Volkova, N. N.; Khabarova, A. A.; El'tsov, O. S. Chem. Heterocycl. Compd. 2013, 48, 1880. [Khim. Geterotsikl. Soedin. 2012, 2002.]Google Scholar
  35. 35.
    Beryozkina, T. V.; Zhidovinov, S. S.; Shafran, Y. M.; Eltsov, O. S.; Slepukhin, P. A.; Leban, J.; Marquez, J.; Bakulev, V. A. Tetrahedron 2014, 70, 3915.CrossRefGoogle Scholar
  36. 36.
    Maruani, A.; Alom, S.; Canavelli, P.; Lee, M. T. W.; Morgan, R. E.; Chudasama, V; Caddick, S. Chem. Commun. 2015, 51, 5279.CrossRefGoogle Scholar
  37. 37.
    Berry, M. T.; Castrejon, D.; Hein, J. E. Org. Lett. 2014, 16, 3676.CrossRefGoogle Scholar
  38. 38.
    Bakulev, V. A.; Beryozkina, T. V.; Tomas, J.; Dehaen, W. Eur. J. Org. Chem. 2018, 262.Google Scholar
  39. 39.
    Murata, S.; Mori, Y.; Satoh, Y.; Yoshidome, R.; Tomioka, H. Chem. Lett. 1999, 597.Google Scholar
  40. 40.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Ilya V. Efimov
    • 1
  • Nikolai A. Beliaev
    • 1
  • Vasiliy A. Bakulev
    • 1
  • Tetyana V. Beryozkina
    • 1
  1. 1.Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St.YekaterinburgRussia

Personalised recommendations