One-pot synthesis of tri- and tetrasubstituted imidazoles using nano-LaMnO3 perovskite-type oxide as reusable heterogeneous catalyst in solvent-free condition

Document Type: Articles

Authors

1 Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.

2 Department of Chemistry, Dezful Branch, Islamic Azad University, Dezful, Iran.

3 Young Researchers and Elite Club, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.

Abstract

A convenient synthetic method for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetra substituted imidazole derivatives, has been developed via one-pot condensation reaction in solvent-free condition when aldehyde, ammonium acetate/amine, and 1,2-diketone are reacted using 0.8 mol% of NP-LaMnO3 at 80 °C under solvent free conditions. Catalyst could be recovered and reused in five reaction cycles without any loss of its activities, giving a total turnover number (TON) = 594 and turn over frequency (TOF) = 71 h−1. High yield, little catalyst loading, elimination of solvent, simple workup, recovery and reusability of the catalyst are some of the impressive features of the present method.

Keywords


[1] Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14 (2004) 541-544.
[2] K. Toshima, R. Takano, T. Ozawa, S. Matsumara, Chem. Commun. 3 (2002) 212-213.
[3] M.R. Grimmett, Comprehensive Heterocyclic Chemistry II, Pergamon, Oxford, 3 (1996) 77–220.
[4] F. Bellina, S. Cauteruccio, R. Rossi, Tetrahedron 63 (2007) 4571-4624.
[5] A.M. Pieczonka, A. Strzelczyk, B. Sadowska, G. Mloston, P. Staczek, Eur. J. Med. Chem. 64 (2013) 389-395.
[6] T.C. Chen, D.S. Yu, K.F. Huang, Y.C. Fu, C.C. Lee, C.L. Chen, F.C. Huang, H.H. Hsieh, J.J. Lin, H.S. Huang, Eur. J. Med. Chem. 69 (2013) 278-293.
[7] H.M. Alkahtani, A.Y. Abbas, S. Wang, Bioorg. Med. Chem. Lett. 22 (2012) 1317-1321.
[8] D. Heinrich, Justus Liebigs Ann. Chem. 107 (1858) 199-208.
[9] B. Radziszewski, Ber. Dtsch. Chem. Ges. 1882, 15, 2706–2708
[10] S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49 (2008) 2216-2220.
[11] H. Zheng, Q.Y. Shi, K. Du, Y.J. Mei, P.F. Zhang, Catal. Lett. 143 (2013) 118-121.
[12] J. Safari, Z. Akbari, S.J. Naseh, J. Saudi Chem. Soc. in press, DOI: http://dx.doi.org/10.1016/j.jscs.2012.10.012
[13] M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 265 (2007) 177-182.
[14] S.N. Murthy, B. Madhav, Y.V.D. Nageswar, Tetrahedron Lett. 51 (2010) 5252-5257.
[15] X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, H.L. Ye, Chin. Chem. Lett. 20 (2009) 44-47.
[16] S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49 (2008) 2216–2220.
[17] G.V. Sharma, Y. Jyothi, P.S. Lakshmi, Synth. Commun. 36 (2006) 2991–3000.
[18] S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem. 266 (2007) 109–113.
[19] B. Sadeghi, B.F. Mirjalili, M.M. Hashemi, Tetrahedron Lett. 49 (2008) 2575–2577.
[20] K. Niknam, A. Deris, F. Naeimi, F. Majleci, Tetrahedron Lett. 52 (2011) 4642–4645.
[21] M.A. Pena, J.L.G. Fierro, Chem. Rev. 101 (2001) 1981-2018.
[22] P. Nabanita, P. Manidipa, B. Asim, Appl. Catal. A 393 (2011) 153-160.
[23] D. Lin, Q. Zheng, Y. Li, Y. Wan, Q. Li, W. Zhou, J. Eur. Ceram. Soc. 33 (2013) 15-24.
[24] J.W. Fergus, Sens. Actuators B 123 (2007) 1169-1179.
[25] T. Sanaeishoar, H. Tavakkoli, F. Mohave, Appl. Catal. A 470 (2014) 470 56-62.
[26] I. Yavari, T. Sanaeishoar, M. Ghazvini, N. Iravani, J. Sulfur Chem. 31 (2010) 169-176.
[27] I. Yavari, T. Sanaeishoar, L. Azad, Mendeleev Commun. 21 (2011) 229-230.
[28] I. Yavari, T. Sanaeishoar, L. Azad, S.J. Arab-Salmanabadi, Chem. Res. (2011) 561-563.
[29] I. Yavari, L. Azad, T. Sanaeishoar, Monatsh. Chem. 142 (2011) 177-182.
[30] H. Naeimi, F. Salimi, K. Rabiei, J. Mol. Catal. A: Chem. 260 (2006) 100-104.
[31] T. Aoyama, S. Murata, T. Takido, M. Kodomari, Tetrahedron 63 (2007) 11933-11937.
[32] L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester, 1995, Vol. 6.
[33] H. Zang, Q. Su, Mo. Yingming, B.W. Cheng, S. Jun, Ultrason. Sonochem. 17 (2010) 749-751.
[34] T. Heinze, T. Liebert, Prog. Polym. Sci. 26 (2001) 1689-1762.
[35] J. Safari, S. Dehghan Khalili, M. Rezaei, S.H. Banitaba, F. Meshkani, Monatsh. Chem. 141 (2010) 1339-1345.
[36] B. Karami, F. Mohammadpour, Croat. Chem. Acta. 85 (2012) 147-153.
[37] K.F. Shelke, S.B. Sapkal, S.S. Sonar, B. Korean, J. Am. Chem. Soc. 30 (2009) 1057-1060.
[38] L. Nagarapu, S. Apuri, S. Kantevari, J. Mol. Catal. A: Chem. 266 (2007) 104-108.
[39] S. Balalaei, A. Arabanian, Green Chem. 2 (2000) 274-276.
[40] S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem. 266 (2007) 109-113.
[41] J. Safari, Z. Zarnegar, C.R. Chim. 16 (2013) 920-928.