Skip to main content
Log in

Recent advances in (hetero)cyclizations of N-vinylazoles (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Recent advances in chemistry of N-vinylazoles are surveyed in this microreview, including results published in the last decade. In particular, reactions involving double bond of N-vinylazoles and formation of new cycles are discussed. These transformations include cycloadditions, cyclopropane syntheses, and heterocyclizations based on the CH activation.

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) Nirmala, M.; Arruri, S.; Vaddamanu, M.; Karupnaswamy, R.; Mannarsamy, M.; Adinarayana, M.; Ganesan, P. Polyhedron 2019, 158, 125. (b) Dhole, S.; Sun, C.-M. Adv. Synth. Cat. 2019, 361, 535. (c) Beck, H.; Jeske, M.; Thede, K.; Stoll, F.; Flamme, I.; Akbaba, M.; Ergüden, J.-K.; Karig, G.; Keldenich, J.; Oehme, F.; Militzer, G.-H.; Hartung, I. V.; Thuss, U. ChemMedChem 2018, 13, 988. (d) He, X.; Zhang, K.; Liu, Y.; Wu, F.; Yu, P.; Mao, L. Angew. Chem., Int. Ed. 2018, 57, 4590. (e) Deng, X.; Shen, J.; Zhu, H.; Xiao, J.; Sun, R.; Xie, F.; Lam, C.; Wang, J.; Qiao, Y.; Tavallaie, M. S.; Hu, Y.; Du, Y.; Li, J.; Fu, L.; Jiang, F. Bioorg. Med. Chem. 2018, 26, 903.

  2. (a) Gusarova, N. K.; Arbuzova, S. N.; Reutskaya, A. M.; Ivanova, N. I.; Baikalova, L. V.; Sinegovskaya, L. M.; Chipanina, N. N.; Afonin, A. V.; Zyryanova, I. A. Chem. Heterocycl. Compd. 2002, 38, 65. [Khim. Geterotsikl. Soedin. 2002, 38, 65.] (b) Gong, T.-J.; Xu, M.-Y.; Yu, S.-H.; Yu, C.-G.; Su, W.; Lu, X.; Xiao, B.; Fu, Y. Org. Lett. 2018, 20, 570. (c) Sun, J.-K.; Kochovski, Z.; Zhang, W.-Y.; Kirmse, H.; Lu, Y.; Antonietti, M.; Yuan, J. J. Am. Chem. Soc. 2017, 139, 8971. (d) Azpiroz, R.; Rubio-Perez, L.; Di Giuseppe, A.; Passarelli, V.; Lahoz, F. J.; Castarlenas, R.; Perez-Torrente, J. J.; Oro, L. A. ACS Catal. 2014, 4, 4244. (e) Saijo, R.; Kawase, M. Eur. J. Org. Chem. 2019, 1535.

  3. Bortolini, O.; De Nino, A.; Eliseo, T.; Gavioli, R.; Maiuolo, L.; Russo, B.; Sforza, F. Bioorg. Med. Chem. 2010, 18, 6970.

    Article  CAS  PubMed  Google Scholar 

  4. Kuprianowicz, M.; Kaźmierczak, M.; Muszyńska, E.; Bzdęga, K.; Wójtowicz-Rajchel, H. J. Fluorine Chem. 2018, 212, 112.

    Article  CAS  Google Scholar 

  5. Piotrowska, D. G.; Cieślak, M.; Królewska, K.; Wróblewski, A. E. Arch. Pharm. 2011, 344, 301.

    Article  CAS  Google Scholar 

  6. Romeo, R.; Giofrè, S. V.; Carnovale, C.; Campisi, A.; Parenti, R.; Bandini, L.; Chiacchio, M. A. Bioorg. Med. Chem. 2013, 21, 7929.

    Article  CAS  PubMed  Google Scholar 

  7. Kallitsakis, M. G.; Carotti, A.; Catto, M.; Peperidou, A.; Hadjipavlou-Litina, D. J.; Litinas, K. E. Open Med. Chem. J. 2017, 11, 196.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Yang, Q.-L.; Xie, M.-S.; Xia, C.; Sun, H.-L.; Zhang, D.-J.; Huang, K.-X.; Guo, Z.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2014, 50, 14809.

    Article  CAS  Google Scholar 

  9. Zhang, D.-J.; Xie, M.-S.; Qu, G.-R.; Gao, Y.-W.; Guo, H.-M. Org. Lett. 2016, 18, 820.

    Article  CAS  PubMed  Google Scholar 

  10. Gao, Y.-W.; Niu, H.-Y.; Zhang, Q.-Y.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Adv. Synth. Catal. 2018, 360, 2813.

    Article  CAS  Google Scholar 

  11. Huang, K.-X.; Xie, M.-S.; Zhao, G.-F.; Qu, G.-R.; Guo, H.-M. Adv. Synth. Catal. 2016, 358, 3627.

    Article  CAS  Google Scholar 

  12. Li, J.-P.; Zhao, G.-F.; Wang, H.-X.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2017, 19, 6494.

    Article  CAS  PubMed  Google Scholar 

  13. Sun, M.; Wu, H.; Zheng, J.; Bao, W. Adv. Synth. Catal. 2012, 354, 835.

    Article  CAS  Google Scholar 

  14. Reddy, V. P.; Iwasaki, T.; Kambe, N. Org. Biomol. Chem. 2013, 11, 2249.

    Article  CAS  PubMed  Google Scholar 

  15. Chen, L.; Zhang, X.; Chen, B.; Li, B.; Li, Y. Chem. Heterocycl. Compd. 2017, 53, 618. [Khim. Geterotsikl. Soedin. 2017, 53, 618.]

  16. Huang, J.-R.; Zhang, Q.-R.; Qu, C.-H.; Sun, X.-H.; Dong, L.; Chen, Y.-C. Org. Lett. 2013, 15, 1878.

    Article  CAS  PubMed  Google Scholar 

  17. Dong, L.; Huang, J.-R.; Qu, C.-H.; Zhang, Q.-R.; Zhang, W.; Han, B.; Peng, C. Org. Biomol. Chem. 2013, 11, 6142.

    Article  CAS  PubMed  Google Scholar 

  18. Thenarukandiyil, R.; Thrikkykkal, H.; Choudhury, J. Organometallics 2016, 35, 3007.

    Article  CAS  Google Scholar 

Download references

Financial support from Enamine Ltd. is acknowledged. The authors thank Prof. Andrey A. Tolmachev for his encouragement and support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Oleksandr O. Grygorenko.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 196–198

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grygorenko, O.O., Nosik, P.S. Recent advances in (hetero)cyclizations of N-vinylazoles (microreview). Chem Heterocycl Comp 55, 196–198 (2019). https://doi.org/10.1007/s10593-019-02440-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02440-6

Navigation