Abstract
A novel (α-Fe2O3)-MCM-41-supported dual acidic ionic liquid (DAIL) catalytic system was prepared. This catalyst was characterized by XRD, TEM, SEM, IR spectra and N2 adsorption–desorption measurements, TGA and acid–base titration. 1-Methyl-3-(4-sulfobutyl) imidazolium hydrogen sulfate as the DAIL inside the mesochannels of α-Fe2O3-MCM-41 led to preparation of a new material which was an efficient magnetic heterogeneous nanocatalyst for one-pot three-component synthesis of some new and known 2-amino-4H-chromenes in water medium conditions. This catalyst was more efficient than other reported catalysts for the synthesis of 2-amino-3-cyano-7-hydroxy-4H-chromenes. High product yields, short reaction times, use of non-corrosives, a robust and reusable magnetic nanocatalyst and water as a green solvent are the most important features of the present work.
Graphical Abstract
Similar content being viewed by others
References
X.M. Liu, M. Liu, X.W. Guo, J.X. Zhou, Catal. Commun. 9, 1 (2010)
Y.Y. Wang, X. Gong, Z. Wang, L.D. Dai, J. Mol. Catal. A: Chem. 322, 7 (2010)
Q. Yang, Z. Wei, H. Zing, Q. Ren, Catal. Commun. 9, 1307 (2008)
A. Riisager, R. Fehrmann, M. Haumann, P. Wasserscheid, Top. Catal. 40, 91 (2006)
S. Rostamizadeh, M. Nojavan, R. Arian, E. Isapoor, M. Azad, J. Mol. Catal. A 374–375, 102 (2013)
M. Curini, G. Cravotto, F. Epifano, G. Giannone, Curr. Med. Chem. 13, 199 (2006)
P.O. Kennedy, R.D. Thornes, Coumarins: biology, applications and mode of action (Wiley, Chichester, 1997)
G.P. Ellis, Chromenes, Cheromenes, and Chromenes, in The chemistry of heterocyclic compounds, ed. by A. Weissberger, E.C. Taylor (Wiley, New York, 1977), pp. 11–139
E.A. Hafez, M.H. Elnagdi, A.G.A. Elagemey, F.M.A.A. El-Taweel, Heterocycles 26, 903 (1987)
A.M. Shestopalov, Y.M. Emelianov, V.N. Nesterov, Russ. Chem. Bull. Int. Ed. 51, 2238 (2002)
D.S. Raghuvanshi, K.N. Singh, ARKIVOC X, 305 (2010)
A. Mobinikhaledi, H. Moghanian, F. Sasani, Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 41, 262 (2011)
S.K. Kunda, J. Mondel, A. Bhaumik, Dalton Trans. 42, 10515 (2013)
B. Datta, M.A. Pasha, Ultrason. Sonochem. 19, 725 (2012)
S. Khaksar, A. Rouhollahpour, S. Mohammadzadeh Talesh, J. Fluor. Chem. 141, 11 (2012)
J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)
S. Rostamizadeh, M. Azad, N. Shadjou, M. Hasanzadeh, Catal. Commun. 25, 83 (2012)
S. Rostamizadeh, N. Shadjou, M. Azad, N. Jalali, Catal. Commun. 26, 218 (2012)
S. Rostamizadeh, M. Nojavan, R. Aryan, M. Azad, Catal. Lett. 144, 1772 (2014)
S. Rostamizadeh, H. Estiri, M. Azad, Catal. Commun. 57, 29 (2014)
M. Abdollahi-Alibeik, M. Pouriayevali, Catal. Commun. 22, 13 (2012)
A. Bordoloi, S. Sahoo, F. Lefevre, S.B. Halligudi, J. Catal. 259, 232 (2008)
Q. Wei, Z. Zhang, Z. Li, Q. Zhou, Y. Zhu, J. Phys. D Appl. Phys. 41, 202002 (2008)
H. Takahashi, B. Li, T. Sasaki, C. Miyazaki, T. Kajino, S. Inagaki, Microporous Mesoporous Mater. 44–45, 755 (2001)
Acknowledgments
We gratefully acknowledge the K. N. Toosi University Research Council for partial financial support of this work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rostamizadeh, S., Zekri, N. An efficient, one-pot synthesis of 2-amino-4H-chromenes catalyzed by (α-Fe2O3)-MCM-41-supported dual acidic ionic liquid as a novel and recyclable magnetic nanocatalyst. Res Chem Intermed 42, 2329–2341 (2016). https://doi.org/10.1007/s11164-015-2152-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2152-9