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.
Similar content being viewed by others
References
Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem.2014, 57, 5845.
(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.
Zhou, J.; Liu, H.; Li, Z.; Jin, C.; Su, W. Tetrahedron Lett.2017, 58, 3174.
(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.
Takahashi, K.; Fukushima, K.; Seto, M.; Togashi, A.; Arai, Y.; Tsubuki, M.; Honda, T. J. Org. Chem.2018, 83, 10636.
Kwiatkowski, M. R.; Alexanian, E. J. Angew. Chem., Int. Ed.2018, 57, 16857.
Wu, C.; Yoshikai, N. Angew. Chem., Int. Ed.2018, 57, 6558.
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.
(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.
Claraz, A.; Serpier, F.; Darses, S. ACS Catal.2017, 7, 3410.
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.
Mori, S.; Shibuya, M.; Yamamoto, Y. Chem. Lett.2017, 46, 207.
Shimkin, K. W.; Montgomery, J. J. Am. Chem. Soc.2018, 140, 7074.
Xia, X.-F.; Yu, J.; Wang, D. Adv. Synth. Catal.2018, 360, 562.
Ye, K.-Y.; Song, Z.; Sauer, G. S.; Harenberg, J. H.; Fu, N.; Lin, S. Chem.–Eur. J.2018, 24, 12274.
Xiang, Y.; Li, Z.; Wang, L.-N.; Yu, Z.-X. J. Org. Chem.2018, 83, 7633.
Borah, M.; Saikia, A. K. ChemistrySelect2018, 3, 2162.
Crespin, L. N. S.; Greb, A.; Blakemore, D. C.; Ley, S. V. J. Org. Chem.2017, 82, 13093.
This work was supported by the Russian Science Foundation (grant 16-13-10023).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(9), 815–817
Rights and permissions
About this article
Cite this article
Smolobochkin, A.V., Gazizov, A.S. Synthesis of 3-arylidenepyrrolidines (microreview). Chem Heterocycl Comp 55, 815–817 (2019). https://doi.org/10.1007/s10593-019-02541-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-019-02541-2