Nano Fe3O4: A Novel and Magnetically Recyclable Catalyst for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles in Solvent-Free Conditions

Naser Montazeri; Khalil Pourshamsian; Hamideh Rezaei; Mahdi Fouladi; Sasan Rahbar

doi:10.14233/ajchem.2013.13963

Issue

Vol. 25 No. 6 (2013): Vol 25 Issue 6

Issue Published : December 26, 2012

This work is licensed under a Creative Commons Attribution 4.0 International License.

Nano Fe3O4: A Novel and Magnetically Recyclable Catalyst for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles in Solvent-Free Conditions

https://doi.org/10.14233/ajchem.2013.13963

Naser Montazeri

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Khalil Pourshamsian

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Hamideh Rezaei

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

Mahdi Fouladi

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran ; Islamic Azad University, Tonekabon Branch, Young Researchers Club, Tonekabon, Iran

Sasan Rahbar

Department of Chemistry, Faculty of Sciences, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran ; Islamic Azad University, Tonekabon Branch, Young Researchers Club, Tonekabon, Iran

Corresponding Author(s) : Naser Montazeri

montazer50@toniau.ac.ir; montazer1350@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 6 (2013): Vol 25 Issue 6
Article Published : January 9, 2013

Abstract

A convenient and efficient one-pot four-component synthesis of 1,2,4,5-tetrasubstituted imidazoles using nano Fe₃O₄ as magnetically recyclable catalyst is reported. The results show that the methodology has several advantages such as low loading of catalyst, excellent yield, short reaction time, operational simplicity and solvent-free conditions.

Keywords

Nano Fe3O4 Tetrasubstituted imidazoles Solvent-free conditions Reusable catalyst

Montazeri, N., Pourshamsian, K., Rezaei, H., Fouladi, M., & Rahbar, S. (2013). Nano Fe3O4: A Novel and Magnetically Recyclable Catalyst for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles in Solvent-Free Conditions. Asian Journal of Chemistry, 25(6), 3463–3466. https://doi.org/10.14233/ajchem.2013.13963

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References

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J.W. Blank, G.J. Durant, J.C. Emmett and C.R. Ganellin, Nature, 248, 65 (1974).
M. Antolini, A. Bozzoli, C. Ghiron, G. Kennedy, T. Rossi and A. Ursini, Bioorg. Med. Chem. Lett., 9, 1023 (1999).
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D. Bourissou, O. Guerret, F.P. Gabbai and G. Bertrand, Chem. Rev., 100, 39 (2000).
(a) R.V.A. Orru and M. de Greef, Synthesis, 1471 (2003); (b) H. Bienayme, C. Hulme, G. Oddon and P. Schmitt, Chem. Eur. J., 6, 3321 (2000).
K. Bahrami, M.M. Khodaei and A. Nejati,Monatsh. Chem., 142, 159 (2011).
N. Tavakoli-Hoseini and A. Davoodnia, Chin. J. Chem., 29, 203 (2011).
A. Davoodnia, M.M. Heravi, Z. Safavi-Rad and N. Tavakoli-Hoseini, Synth. Commun., 40, 2588 (2010).
A.R. Karimi, Z. Alimohammadi, J. Azizian,A.A. Mohammadi and M.R. Mohammadizadeh, Catal. Commun., 7, 728 (2006).
L. Nagarapu, S. Apuri and S. Kantevari, J. Mol. Catal. A, 266, 104 (2007).
B. Sadeghi, B.B.F. Mirjalili and M.M. Hashemi, Tetrahedron Lett., 49, 2575 (2008).
M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey and T.P. Singh, J. Mol. Catal. A., 265, 177 (2006).
S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar and L. Nagarapu, J. Mol. Catal. A, 266, 109 (2007).
S. Samai, G.C. Nandi, P. Singh and M.S. Singh, Tetrahedron, 65, 10155 (2009).
S. Balalaie, M.M. Hashemi and M. Akhbari, Tetrahedron Lett., 44, 1709 (2003).
I. Lantos, W.Y. Zhang, Y. Shui and D.S. Eggleston, J. Org. Chem., 58, 7092 (1993).
C.F. Claiborne, N.J. Liverton and K.T. Nguyen, Tetrahedron Lett., 39, 8939 (1998).
(a) F. Shi, M.K. Tse, S.L. Zhou, M.M. Pohl, J. Radnik, S. Hubner, K. Jahnisch, A. Bruckner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); (b) M.J. Aliaga, D.J. Ramon and M. Yus, Org. Biomol. Chem., 8, 43 (2010).
(a) V. Polshettiwar, B. Baruwati and R.S. Varma, Chem. Commun., 1837 (2009); (b) V. Polshettiwar and R.S. Varma,Chem. Eur. J., 15, 1582 (2009).
(a) B. Sreedhar, A.S. Kumar and P.S. Reddy, Tetrahedron Lett., 50, 2322 (2009); (b) M.M. Mojtahedi, M.S. Abaee and T. Alishiri, Tetrahedron Lett., 50, 2322 (2009).
(a) N. Montazeri and K. Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008); (b) N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011); (c) N. Montazeri and K. Rad-Moghadam, Phosphorus, Sulfur, Silicon Rel. Elem., 179, 2533 (2004).

References

M. Misono, Chem. Commun., 1141 (2001).

J.W. Blank, G.J. Durant, J.C. Emmett and C.R. Ganellin, Nature, 248, 65 (1974).

M. Antolini, A. Bozzoli, C. Ghiron, G. Kennedy, T. Rossi and A. Ursini, Bioorg. Med. Chem. Lett., 9, 1023 (1999).

L. Wang, K.W. Woods, Q. Li, K.J. Barr, R.W. McCroskey, S.M. Hannick, L. Gherke, R.B. Credo, Y.-H. Hui, K. Marsh, R. Warner, J.Y. Lee, N. Zielinsky-Mozng, D. Frost, S.H. Rosenberg and H.L. Sham, J. Med. Chem., 45, 1697 (2002).

R. Schmierer, H. Mildenberger and H. Buerstell, Ger 3614364, (1987); Chem. Abstr., 108, 37838 (1988).

S.E. De Laszlo, C. Hacker, B. Li, D. Kim, M. MacCoss, N. Mantlo, J.V. Pivnichny, L. Colwell, G.E. Koch, M.A. Cascieri and W. Hagmann, Bioorg. Med. Chem. Lett., 9, 641 (1999).

S. Chowdhury, R.S. Mohan and J.L. Scott, Tetrahedron, 63, 2363 (2007).

D. Bourissou, O. Guerret, F.P. Gabbai and G. Bertrand, Chem. Rev., 100, 39 (2000).

(a) R.V.A. Orru and M. de Greef, Synthesis, 1471 (2003); (b) H. Bienayme, C. Hulme, G. Oddon and P. Schmitt, Chem. Eur. J., 6, 3321 (2000).

K. Bahrami, M.M. Khodaei and A. Nejati,Monatsh. Chem., 142, 159 (2011).

N. Tavakoli-Hoseini and A. Davoodnia, Chin. J. Chem., 29, 203 (2011).

A. Davoodnia, M.M. Heravi, Z. Safavi-Rad and N. Tavakoli-Hoseini, Synth. Commun., 40, 2588 (2010).

A.R. Karimi, Z. Alimohammadi, J. Azizian,A.A. Mohammadi and M.R. Mohammadizadeh, Catal. Commun., 7, 728 (2006).

L. Nagarapu, S. Apuri and S. Kantevari, J. Mol. Catal. A, 266, 104 (2007).

B. Sadeghi, B.B.F. Mirjalili and M.M. Hashemi, Tetrahedron Lett., 49, 2575 (2008).

M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey and T.P. Singh, J. Mol. Catal. A., 265, 177 (2006).

S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar and L. Nagarapu, J. Mol. Catal. A, 266, 109 (2007).

S. Samai, G.C. Nandi, P. Singh and M.S. Singh, Tetrahedron, 65, 10155 (2009).

S. Balalaie, M.M. Hashemi and M. Akhbari, Tetrahedron Lett., 44, 1709 (2003).

I. Lantos, W.Y. Zhang, Y. Shui and D.S. Eggleston, J. Org. Chem., 58, 7092 (1993).

C.F. Claiborne, N.J. Liverton and K.T. Nguyen, Tetrahedron Lett., 39, 8939 (1998).

(a) F. Shi, M.K. Tse, S.L. Zhou, M.M. Pohl, J. Radnik, S. Hubner, K. Jahnisch, A. Bruckner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); (b) M.J. Aliaga, D.J. Ramon and M. Yus, Org. Biomol. Chem., 8, 43 (2010).

(a) V. Polshettiwar, B. Baruwati and R.S. Varma, Chem. Commun., 1837 (2009); (b) V. Polshettiwar and R.S. Varma,Chem. Eur. J., 15, 1582 (2009).

(a) B. Sreedhar, A.S. Kumar and P.S. Reddy, Tetrahedron Lett., 50, 2322 (2009); (b) M.M. Mojtahedi, M.S. Abaee and T. Alishiri, Tetrahedron Lett., 50, 2322 (2009).

(a) N. Montazeri and K. Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008); (b) N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011); (c) N. Montazeri and K. Rad-Moghadam, Phosphorus, Sulfur, Silicon Rel. Elem., 179, 2533 (2004).

Issue

Vol. 25 No. 6 (2013): Vol 25 Issue 6

Nano Fe3O4: A Novel and Magnetically Recyclable Catalyst for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles in Solvent-Free Conditions

Corresponding Author(s) : Naser Montazeri

Abstract

Keywords

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