Advertisement

Chemistry of Heterocyclic Compounds

, Volume 55, Issue 9, pp 815–817 | Cite as

Open image in new window Synthesis of 3-arylidenepyrrolidines (microreview)

  • Andrey V. SmolobochkinEmail author
  • Almir S. Gazizov
Article
  • 32 Downloads

The review summarizes methods of synthesis of 3-arylidenepyrrolidines, illustrated by the most typical examples, published in 2017–2019. The methods are divided into three main groups: modification of the 1-pyrroline (pyrrolidine) ring, intramolecular and intermolecular cyclization of unsaturated acyclic precursors.

Notes

This work was supported by the Russian Science Foundation (grant 16-13-10023).

References

  1. 1.
    Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem.2014, 57, 5845.CrossRefGoogle Scholar
  2. 2.
    (а) Delong, W.; Lanying, W.; Yongling, W.; Shuang, S.; Juntao, F.; Xing, Z. Eur. J. Med. Chem.2017, 130, 286. (b) Lorente, A.; Pla, D.; Cañedo, L. M.; Albericio, F.; Álvarez, M. J. Org. Chem.2010, 75, 8508. (c) Denmark, S. E.; Liu, J. H.-C.; Muhuhi, J. M. J. Am. Chem. Soc.2009, 131, 14188. (d) Ranatunga, S.; Tang, C.-H. A.; Hu, C.-C. A.; Del Valle, J. R. J. Org. Chem.2012, 77, 9859.Google Scholar
  3. 3.
    Zhou, J.; Liu, H.; Li, Z.; Jin, C.; Su, W. Tetrahedron Lett.2017, 58, 3174.CrossRefGoogle Scholar
  4. 4.
    (a) Smolobochkin, A. V.; Gazizov, A. S.; Melyashova, A. S.; Voronina, J. K.; Strelnik, A. G.; Vatsadze, S. Z.; Burilov, A. R.; Pudovik, M. A.; Fedorova, O. A.; Sinyashin, O. G. RSC Adv.2017, 7, 50955. (b) Smolobochkin, A. V.; Melyashova, A. S.; Gazizov, A. S.; Burilov, A. R.; Pudovik, M. A. Russ. J. Gen. Chem.2018, 88, 1934. [Zh. Obshch. Khim.2018, 88, 1566.] (c) Dwari, S.; Jana, C. K. ACS Omega2019, 4, 2445.Google Scholar
  5. 5.
    Takahashi, K.; Fukushima, K.; Seto, M.; Togashi, A.; Arai, Y.; Tsubuki, M.; Honda, T. J. Org. Chem.2018, 83, 10636.CrossRefGoogle Scholar
  6. 6.
    Kwiatkowski, M. R.; Alexanian, E. J. Angew. Chem., Int. Ed.2018, 57, 16857.Google Scholar
  7. 7.
    Wu, C.; Yoshikai, N. Angew. Chem., Int. Ed.2018, 57, 6558.Google Scholar
  8. 8.
    Li, M.; Wang, C.-T.; Qiu, Y.-F.; Zhu, X.-Y.; Han, Y.-P.; Xia, Y.; Li, X.-S.; Liang, Y.-M. Chem. Commun.2018, 54, 5334.CrossRefGoogle Scholar
  9. 9.
    (a) Cabrera-Lobera, N.; Quirós, M. T.; Buñuel, E.; Cárdenas, D. J. Catal. Sci. Technol.2019, 9, 1021. (b) Cabrera-Lobera, N.; Rodríguez-Salamanca, P.; Nieto-Carmona, J. C.; Buñuel, E.; Cárdenas, D. J. Chem.–Eur. J.2018, 24, 784.Google Scholar
  10. 10.
    Claraz, A.; Serpier, F.; Darses, S. ACS Catal.2017, 7, 3410.CrossRefGoogle Scholar
  11. 11.
    Yap, C.; Lenagh-Snow, G. M. J.; Karad, S. N.; Lewis, W.; Diorazio, L. J.; Lam, H. W. Angew. Chem., Int. Ed.2017, 56, 8216.Google Scholar
  12. 12.
    Mori, S.; Shibuya, M.; Yamamoto, Y. Chem. Lett.2017, 46, 207.CrossRefGoogle Scholar
  13. 13.
    Shimkin, K. W.; Montgomery, J. J. Am. Chem. Soc.2018, 140, 7074.CrossRefGoogle Scholar
  14. 14.
    Xia, X.-F.; Yu, J.; Wang, D. Adv. Synth. Catal.2018, 360, 562.CrossRefGoogle Scholar
  15. 15.
    Ye, K.-Y.; Song, Z.; Sauer, G. S.; Harenberg, J. H.; Fu, N.; Lin, S. Chem.–Eur. J.2018, 24, 12274.CrossRefGoogle Scholar
  16. 16.
    Xiang, Y.; Li, Z.; Wang, L.-N.; Yu, Z.-X. J. Org. Chem.2018, 83, 7633.CrossRefGoogle Scholar
  17. 17.
    Borah, M.; Saikia, A. K. ChemistrySelect2018, 3, 2162.CrossRefGoogle Scholar
  18. 18.
    Crespin, L. N. S.; Greb, A.; Blakemore, D. C.; Ley, S. V. J. Org. Chem.2017, 82, 13093.CrossRefGoogle Scholar

Copyright information

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

Authors and Affiliations

  1. 1.Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Federal Research CenterRussian Academy of SciencesKazanRussia

Personalised recommendations