Abstract
A supported ionic liquid ILCF3SO3@SiO2 was synthesized and used as a highly efficient catalyst in the Paal–Knorr reaction for the preparation of pyrroles. The heterogeneous catalyst could be easily recovered and recycled for five times without noticeable loss of catalytic activity. Also a possible reaction mechanism is provided.
Graphical Abstract
Similar content being viewed by others
References
B. Pacorel, S.C. Leung, A.V. Stachulski, J. Davies, L. Vivas, H. Lander, S.A. Ward, M. Kaiser, R. Brun, P.M. O’Neill, J. Med. Chem. 53, 633 (2010)
V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Soc. Rev. 39, 4402 (2010)
N. Yoshikai, Y. Wei, Asian J. Org. Chem. 2, 466 (2013)
S.E. Drewes, C.J. Hogan, Synth. Commun. 19, 2101 (1989)
S. Raghavan, K. Anuradha, Synlett 2003, 711 (2003)
K. Aghapoor, L. Ebadi-Nia, F. Mohsenzadeh, M.M. Morad, Y. Balavar, H.R. Darabi, J. Organomet. Chem. 708–709, 25 (2012)
V.S.V. Satyanarayana, A. Sivakumar, Ultrason. Sonochem. 18, 917 (2011)
J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, W. Su, Tetrahedron Lett. 47, 5383 (2006)
I. Bianchi, R. Forlani, G. Minetto, I. Peretto, N. Regalia, M. Taddei, L.F. Raveglia, J. Comb. Chem. 8, 491 (2006)
G. Yin, Z. Wang, A. Chen, M. Gao, A. Wu, Y. Pan, J. Org. Chem. 73, 3377 (2008)
G.E. Veitch, K.L. Bridgwood, K. Rands-Trevor, S.V. Ley, Synlett 2008, 2597 (2008)
N.T.S. Phan, T.T. Nguyen, Q.H. Luu, L.T.L. Nguyen, J. Mol. Catal. A Chem. 363–364, 178 (2012)
P. Cheng, W. Shao, D.L.J. Clive, J. Org. Chem. 78, 11860 (2013)
X. Zhang, G. Weng, Y. Zhang, P. Li, Tetrahedron 71, 2595 (2015)
S.K. Pasha, V.S.V. Satyanarayana, A. Sivakumar, K. Chidambaram, L.J. Kennedy, Chin. Chem. Lett. 22, 891 (2011)
P.B. Cranwell, M. O’Brien, D.L. Browne, P. Koos, A. Polyzos, M. Peña-López, S.V. Ley, Org. Biomol. Chem. 10, 5774 (2012)
H. Veisi, Tetrahedron Lett. 51, 2109 (2010)
B.H. Kim, S. Bae, A. Go, H. Lee, C. Gong, B.M. Lee, Org. Biomol. Chem. 14, 265 (2016)
H. Cho, R. Madden, B. Nisanci, B. Török, Green Chem. 17, 1088 (2015)
D. Bandyopadhyay, E. Rhodes, B.K. Banik, RSC Adv. 3, 16756 (2013)
O. Goli-Jolodar, F. Shirini, J. Iran. Chem. Soc. 13, 1077 (2016)
B.V.D. Vijaykumar, B. Premkumar, K. Jang, B.I. Choi, J.R. Falck, G.N. Sheldrake, D.S. Shin, Green Chem. 16, 2406 (2014)
L. Sheikhian, M. Shirafkan, J. Iran. Chem. Soc. 13, 903 (2016)
N. Farzadbeh, M.T. Vardini, H. Sheikhloie, J. Iran. Chem. Soc. 13, 715 (2016)
B. Wang, Y. Gu, C. Luo, T. Yang, L. Yang, J. Suo, Tetrahedron Lett. 45, 3417 (2004)
N. Gupta, K.N. Singh, J. Singh, J. Mol. Liq. 199, 470 (2014)
H.C. Hu, Y.H. Liu, B.L. Li, Z.S. Cui, Z.H. Zhang, RSC Adv. 5, 7720 (2015)
D. Li, H. Zang, C. Wu, N. Yu, Ultrason. Sonochem. 20, 1144 (2013)
R. Hajian, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 13, 1061 (2016)
C. Fehér, E. Kriván, J. Hancsók, R. Skoda-Földes, Green Chem. 14, 403 (2012)
N. Candu, C. Rizescu, I. Podolean, M. Tudorache, V.I. Parvulescu, S.M. Coman, Catal. Sci. Technol. 5, 729 (2015)
A.M. Lazarin, Y. Gushikem, S.C. de Castro, J. Mater. Chem. 10, 2526 (2000)
M. Vafaeezadeh, M.M. Hashemi, Chem. Eng. J. 250, 35 (2014)
W. Ding, W. Zhu, J. Xiong, L. Yang, A. Wei, M. Zhang, H. Li, Chem. Eng. J. 266, 213 (2015)
Acknowledgements
We express our thanks to the Natural Science Foundation of China (No. 21506115) and the Research Foundation of Yichang Science and Technology Bureau (No. A15-302-a03) for financial assistance.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Liu, Y., Hu, Y.L. Novel and highly efficient preparation of pyrroles using supported ionic liquid ILCF3SO3@SiO2 as a heterogeneous catalyst. J IRAN CHEM SOC 15, 1033–1040 (2018). https://doi.org/10.1007/s13738-018-1300-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-018-1300-8