Improving methodology for the preparation of highly substituted imidazoles using nano-MgAl2O4 as catalyst under microwave irradiation

Subject Areas : Iranian Journal of Catalysis

Javad Safari ¹ , Soheila Gandomi-Ravandi ² , Zahra Akbari ³

1 - Laboratory of Organic Chemistry Research, Department of Chemistry, College of Chemistry, University of Kashan, Kashan, P.O. Box: 87317-51167, Kashan, Islamic Republic of Iran.
2 - Laboratory of Organic Chemistry Research, Department of Chemistry, College of Chemistry, University of Kashan, Kashan, P.O. Box: 87317-51167, Kashan, Islamic Republic of Iran.
3 - Laboratory of Organic Chemistry Research, Department of Chemistry, College of Chemistry, University of Kashan, Kashan, P.O. Box: 87317-51167, Kashan, Islamic Republic of Iran.

Received: 2013-02-05 Accepted : 2013-05-10 Published : 2013-03-01

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References:

[1] (a) K.M. El-Shaieb, Heteroat. Chem. 17 (5) (2006) 365–368. (b) M. Fantini, V. Zulini, M.A. Spotti, M. Rivara, J. Comb. Chem. 12 (1) (2010) 181–185. (c) K. Shelke, G. Kakade, B. Shingate, M. Shingare, Rasayan J. Chem. 1 (2008) 489–494. (d) G.W. Gribble, J.A. Joule, Progress in Heterocyclic Chemistry, Eds Elsevier, 2009, 26, 232.
[2] (a) G. Xu, Y.G. Wang, Org. Lett. 6 (6) (2004) 985–987. (b) A.L.D. Hoz, A. Diaz-Ortiz, A. Moreno, Curr. Org. Chem. 8 (10) (2004) 903–918.
[3] D.E. Golan, A.W. Armstrong, Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy, Wolters Kluwer Health, 2007.
[4] N.R. Bhat, P.S. Zhang, S.B. Mohanty, Neurochem. Res. 32 (2007) 293–302.


[5] S.L. Gaonkar, K.M. Lokanatha Rai, N. Suchetha Shetty, Med. Chem. Res. 18 (2009) 221–230.
[6] M.S. Sham, J. Shubhi, D. Monica, K. Ashok, Med. Chem. 4 (2008) 146–154.
[7] F. Bellina, S. Cauteruccio, S. Montib, R. Rossi, Bioorg. Med. Chem. Lett. 16 (2006) 5757–5762.
[8] M. Misono, Chem. Commun. (2001) 1141–1152.
[9] Q. Zhao, S.J. Liu, M. Shi, F.Y. Li, H. Jing, T. Yi, Organometallics 26 (2007) 5922–5930.
[10] W. Peter, K. Wilhelm, Angew. Chem. Int. Edit. 39 (2000) 3772–3789.
[11] A. Satake, M. Fujita, Y. Kurimotoa, Y. Kobuke, Chem. Commun. (2009) 1231–1233.
[12] K. Kameyama, A. Satake, Y. Kobuke, Tetrahedron Lett. 45 (2004) 7617–7620.
[13] N. Nagata, S. Kugimiya, Y. Kobuke, Chem. Commun. (2000) 1389–1390.
[14] M. Morisue, K. Ogawa, K. Kamada, K. Ohtab, Y. Kobuke, Chem. Commun. 46 (2010) 2121–2123.
[15] J.Y. Liu, P.C. Lo, D.K.P. Ng, Struct. Bond. 135 (2010) 169–210.
[16] K. Ogawa, A. Ohashi, Y. Kobuke, K. Kamada, K. Ohta, J. Phys. Chem. B. 109 (2005) 22003–22012.
[17] Y. Miyazaki, A. Satake, Y. Kobuke, J. Mol. Catal. A. Chem. 283 (2008) 129–139.
[18] F. Bellina, S. Cauteruccio, R. Rossi, Tetrahedron 63 (2007) 4571–4624.
[19] S. Park, O.H. Kwon, S. Kim, S. Park, M.G. Choi, M. Cha, S.Y. Park, D.J. Jang, J. Am. Chem. Soc. 127 (2005) 10070–10074.
[20] Y.F. Sun, Y.P. Cui, Dyes Pigm. 81 (2009) 27–34.
[21] Y.F. Sun, W. Huang, C.G. Lu, Y.P. Cui, Dyes Pigm. 81 (2009) 10–17.
[22] H.J. Zhu, J.S. Wang, K.S. Patrick, J.L. Donovan, C.L. DeVane, J.S. J. Markowitz, B. Chromatogr, Anal. Technol. Biomed. Life Sci. 858 (2007) 91–95.
[23] K. Nakashima, H. Yamasaki, N. Kuroda, S. Akiyama, Anal. Chim. Acta 303 (1995) 103–107.
[24] N. Kuroda, R. Shimoda, M. Wada, K. Nakashima, Anal. Chim. Acta 403 (2000) 131–136.
[25] M. Staehelin, D.M. Burland, M. Ebert, R.D. Miller, B.A. Smith, R.J. Twieg, W. Volksen, C.A. Walsh, Appl. Phys. Lett. 61 (1992) 1626–1628.
[26] D. Davidson, M. Weiss, M. Jelling, J. Org. Chem. 2 (1937) 319–327.
[27] R. Conssoni, P.D. Croce, R. Ferraccioli, L.A. Rosa J. Chem. Res. (s) (1991) 188–189.
[28] C.F. Claiborne, N.J. Liverton, K.T. Nguyen, Tetrahedron Lett. 39 (1998) 8939–8842.
[29] A. Teimouri, A.N. Chermahini, J. Mol. Catal. A: Chem. 346 (2011) 39–45.
[30] B.F. Mirjalili, A.H. Bamoniri, L. Zamani, Sci. Iran. 19 (3) (2012) 565–568.
[31] (a) D.A. Evans, K.M. Lundy, J. Am. Chem. Soc. 114 (4) (1992) 1495–1496. (b) P. Schneiders, J. Heinze, H. Baumgartel, Chem. Ber. 106 (1973) 2415–2417.
[32] E.N. Alvar, M. Rezaei, H.N. Alvar, Powder Technol. 198 (2010) 275–278.
[33] A.R. Khosropour, Ultrason. Sonochem. 15 (2008) 659–664.
[34] X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, H.L. Ye, Chin. Chem. Lett. 20 (2009) 44–47.
[35] S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49 (2008) 2216–2220.
[36] A. Teimouria, A. Najafi Chermahini, J. Mol. Catal. A: Chem. 346 (2011) 39–45.
[37] M.M. Khodaei, K. Bahrami, I. Kavianinia, J. Chin. Chem. Soc. 54 (2007) 829–833.
[38] A. Shaabani, A. Rahmati, J. Mol. Catal. A: Chem. 249 (2006) 246–248.
[39] A. Shaabani, A. Maleki, M. Behnam, Synth. Commun. 39 (2009) 102–110.
[40] H. Zang, Q. Su, Y. Mo, B. Cheng, S. Jun, Ultrason. Sonochem. 17 (2010) 749–751.
[41] A. Teimouria, A. Najafi Chermahini, J. Mol. Catal. A Chem. 346 (2011) 39–45.
[42] A. Shaabani, A. Rahmati, J. Mol. Catal. A Chem. 249 (2006) 246.
[43] X.C. Wang, H.P. Gong, Z.J. Quan, L. Li, H.L. Ye, Chin. Chem. Lett. 20 (2009) 44–47.
[44] M.G. Shen, C. Cai, W.B. Yi, J. Fluorine Chem. 129 (2008) 541–544.
[45] K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Let. Rev. 3 (2010) 27–32.
[46] M.R. Grimett, In Comprehensive Heterocyclic Chemistry II; A.R. Katritzky, C.W. Rees, E.F. Scriven, New York: Pergamon, 3 (1996) 77.
[47] F. Meshkani, M. Rezaei, Powder Technol. 196 (2009) 85–88.