Abstract
A novel acidic ionic liquid based on imidazoliumcation is designed, synthesized, and successfully used as a catalyst for the one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole derivatives. The remarkable feature of this new catalyst is its ethyleneoxy bridge which participates in dissolving organic compounds in ionic liquids. The application of this acidic ionic liquid is studied in a new one-pot method for the synthesis of imidazole derivatives under solvent-free conditions. The advantages of this method are the reusability of the catalyst, high conversion, short reaction time, and simple experimental procedure.
Similar content being viewed by others
References
P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis (Wiley, Weinheim, 2008)
W. Keim, P. Wasserscheid, Angew. Chem. Int. Ed. 39, 3772 (2000)
N. Jain, A. Kumar, S. Chauhan, S.M.S. Chauhan, Tetrahedron 61, 1015 (2005)
Y. Gu, F. Shi, Y. Deng, J. Org. Chem. 69, 391 (2004)
B.C. Ranu, R. Jana, J. Org. Chem. 70, 8621 (2005)
N.E. Leadbeater, H.M. Torenius, J. Org. Chem. 67, 3145 (2002)
R. Sheldon, Chem. Commun. 2399 (2001)
T. Welton, Coord. Chem. Rev. 248, 2459 (2004)
A. Chetia, C.J. Saikia, K.C. Lekhok, R.C. Boruah, Tetrahedron Lett. 45, 2649 (2004)
A. D¨omling, I. Ugi, Angew. Chem. Int. Ed. 39, 3169 (2000)
M. Kidwai, P. Mothsra, V. Bansal, R. Goyal, Monatsh. Chem. 137, 1189 (2006)
W. Lin, L. Long, L. Yuan, Z. Cao, B. Chen, W. Tan, Org. Lett. 10, 5577 (2008)
Y. Ooyama, K. Uwada, H. Kumaoka, K. Yoshida, Eur. J. Org. Chem. 34, 5979 (2009)
L.M. Wang, Y.H. Wang, H. Tian, Y.F. Yao, J.H. Shao, B. Liu, J. Fluor. Chem. 127, 1570 (2006)
K. Srinivas, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A 266, 109 (2007)
S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61, 3539 (2005)
J.L. Anderson, R. Ding, A. Ellern, D.W. Armstrong, J. Am. Chem. Soc. 127, 593 (2005)
S. Chowdhury, R.S. Mohan, J.L. Scott, Tetrahedron 63, 2363 (2007)
J.P. Hallett, T. Walton, Chem. Rev. 111, 3508 (2011)
W. Liu, C. Ye, Q. Gong, H. Wang, P. Wang, Tribol. Lett. 13, 81 (2002)
Q. Liu, F.V. Rantwijk, R.A. Sheldon, J. Chem. Technol. Biotechnol. 81, 401 (2006)
Y.S. Ding, M. Zha, J. Zhang, S.S. Wang, Colloids Surf. A 298, 201 (2007)
A.H. Jadhav, H. Kim, Chem. Eng. J. 200–202, 264 (2012)
T.L. Greaves, C.J. Drummond, Chem. Rev. 108, 206 (2008)
R. Kore, R. Srivastava, J. Mol. Catal. A 345, 117 (2011)
H.R. Shaterian, M. Ranjbar, K. Azizi, J. Iran. Chem. Soc. 8, 1120 (2011)
A.S. Edgar, R.D. Allan, J. Am. Chem. Soc. 68, 771 (1946)
S. Damavandi, Heterocycl. Commun. 17, 79 (2011)
Y. Ishida, D. Sasaki, H. Miyauchi, K. Saigo, Tetrahedron Lett. 45, 9455 (2004)
Z. Zeng, B.S. Phillips, J. Xiao, J.M. Shreeve, Chem. Mater. 20, 2719 (2008)
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone et al., Gaussian 09, Revision A.1 (Gaussian, Inc., Wallingford, 2009)
A.S. Edgar, R.D. Allan, J. Am. Chem. Soc. 65, 452 (1943)
S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65, 10155 (2009)
Acknowledgment
We are grateful to Ferdowsi University of Mashhad Research Council for their financial support of this work (GN: 3/28349).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Eshghi, H., Rahimizadeh, M., Hasanpour, M. et al. A novel imidazolium-based acidic ionic liquid as an efficient and reusable catalyst for the synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazoles. Res Chem Intermed 41, 4187–4197 (2015). https://doi.org/10.1007/s11164-013-1522-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1522-4