This microreview describes the progress and results of the update reports in the synthesis of pyrrole skeletons using propargylamine, its derivatives, and in situ formed propargylamine as a building block. Both transition metal-catalyzed and metal-free synthetic strategies have been discussed.
Similar content being viewed by others
References
(a) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264. (b) Young, I. S.; Thornton, P. D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801. (c) Khramtsova, E. E.; Dmitriev, M. V.; Bormotov, N. I.; Serova, O. А.; Shishkina, L. N.; Maslivets, A. N. Chem. Heterocycl. Compd. 2021, 57, 483.
(a) Curran, D.; Grimshaw, J.; Perera, S. D. Chem. Soc. Rev. 1991, 20, 391. (b) Zelina, E. Yu. Chem. Heterocycl. Compd. 2021, 57, 990. (c) Li, C.-S.; Tsai, Y.-H.; Lee, W.-C.; Kuo, W.-J. J. Org. Chem. 2010, 75, 4004. (d) Facchetti, A.; Abbotto, A.; Beverina, L.; van der Boom, M. E.; Dutta, P.; Evmenenko, G.; Pagani, G. A.; Marks, T. J. Chem. Mater. 2003, 15, 1064.
(a) Trofimov, B. A.; Schmidt, E. Yu. Acc. Chem. Res. 2018, 51, 1117. (b) Lauder, K.; Toscani, A.; Scalacci, N.; Castagnolo, D. Chem. Rev. 2017, 117, 14091. (c) Chelucci, G. Coord. Chem. Rev. 2017, 331, 37. (d) Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2014, 43, 4633.
Neto, J. S. S.; Zeni, G. ChemCatChem 2020, 12, 3335.
(a) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008, 10, 2629. (b) Saito, A.; Konishi, T.; Hanzawa, Y. Org. Lett. 2010, 12, 372. (c) Yang, X.; Wang, Y.; Hu, F.; Kan, X.; Yang, C.; Liu, J.; Liu, P.; Zhang, Q. RSC Adv. 2016, 6, 68454.
Kanova, N.; Dundar, B. A.; Kelgokmen, Y.; Zora, M. J. Org. Chem. 2021, 86, 6289.
Behera, B. K.; Sahu, A. K.; Devi, N. R.; Saikia, A. K. J. Org. Chem. 2021, 86, 12481.
(a) Xu, X. J.; Feng, H. D.; Van der Eycken, E. V. Org. Lett. 2021, 23, 6578. (b) Feng, H. D.; Wang, F.; Cao, L. L.; Van der Eycken, E. V.; Yin, X. Y. Eur. J. Org. Chem. 2021, 3676. (c) Cao, L. L.; Zhou, P. Y.; Hu, J. D.; Huang, L. L.; Feng, H. D. ChemistrySelect 2022, 7, e202200200.
Xu, X. J.; Feng, H. D.; Zhang, X. Y.; Song, L. L.; Van Meervelt, L.; Van der Eycken, J.; Harvey, J. N.; Van der Eycken, E. V. Org. Lett. 2022, 24, 1232.
(a) Ge, B.; Lv, W.; Yu, J.; Xiao, S.; Cheng, G. Org. Chem. Front. 2018, 5, 3103. (b) Cheng, G.; Lv, W.; Xue, L. Green Chem. 2018, 20, 4414.
(a) Golantsov, N. E.; Golubenkova, A. S.; Festa, A. A.; Varlamov, A. V.; Voskressensky, L. G. Org. Lett. 2020, 22, 4726. (b) Golantsov, N. E.; Golubenkova, A. S.; Festa, A. A.; Varlamov, A. V.; Voskressensky, L. G. J. Org. Chem. 2022, 87, 3242.
Mishra, P. K.; Verma, S.; Kumar, M.; Verma, A. K. Org. Lett. 2018, 20, 7182.
Ye, C.; Jiao, Y.; Chiou, M.-F.; Li, Y.; Bao, H. Chem. Sci. 2021, 12, 9162.
Chen, L.; Huo, J.-Q.; Si, H.-L.; Xu, X.-Y.; Kou, S.; Mao, J. Y.; Zhang, J.-L. Org. Lett. 2021, 23, 4348.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 193–195
Rights and permissions
About this article
Cite this article
Gong, J., Feng, H. Synthesis of pyrroles from propargylamines and their derivatives: an update (microreview). Chem Heterocycl Comp 58, 193–195 (2022). https://doi.org/10.1007/s10593-022-03071-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-022-03071-0