Abstract
In this paper, one-pot synthesis of 2,4,6-triarylpyridine by condensation of subsisted acetophenone (II), aromatic aldehydes (I), and ammonium acetate (III) in the presence of nanocrystalline MgAl2O4 as a new heterogeneous catalyst under solvent-free conditions is reported. Advantages of this method are the use of spatially-hindered aldehydes such as 2-methoxy-, 2-fluoro-, and 2-chlorobenzaldehydes, a new nanocatalyst with high surface area, shorter reaction time, easier workup, higher yield, and its environmental friendliness. The performance of this reaction under solvent free conditions using heterogeneous catalysts like MgAl2O4 could enhance its efficiency from an economic as well as green chemistry point of view.
Similar content being viewed by others
References
Adib, M., Tahermansouri, H., Koloogani, S. A., Mohammadi, B., & Bijanzadeh, H. R. (2006). Kröhnke pyridines: an efficient solvent-free synthesis of 2,4,6-triarylpyridines. Tetrahedron Letters, 47, 5957–5960. DOI: 10.1016/j.tetlet.2006.01.162.
Banerjee, S., & Sereda, G. (2009). One-step, three-component synthesis of highly substituted pyridines using silica nanoparticle as reusable catalyst. Tetrahedron Letters, 50, 6959–6962. DOI: 10.1016/j.tetlet.2009.09.137.
Barluenga, J., Jiménez-Aquino, A., Fernández, M. A., Aznar, F., & Valdés, C. (2008). Multicomponent and one-pot synthesis of trisubstituted pyridines through a Pd-catalyzed crosscoupling/ cross-coupling/cycloaddition sequence. Tetrahedron, 64, 778–786. DOI: 10.1016/j.tet.2007.10.112.
Chiu, C. F., Tang, Z. L., & Ellingboe, J. W. (1998). Solid-phase synthesis of 2,4,6-trisubstituted pyridines. Journal of Combinatorial Chemistry, 1, 73–77. DOI: 10.1021/cc980005g.
Constable, E. C., Housecroft, C. E., Neuburger, M., Phillips, D., Raithby, P. R., Schofield, E., Sparr, E., Tocher, D. A., Zehnder, M., & Zimmermann, Y. (2000). Development of supramolecular structure through alkylation of pendant pyridyl functionality. Journal of Chemical Society, Dalton Transactions, 13, 2219–2228. DOI: 10.1039/b000940g.
Davoodnia, A., Bakavoli, M., Moloudi, R., Tavakoli-Hoseini, N., & Khashi, M. (2010). Highly efficient, one-pot, solvent-free synthesis of 2,4,6-triarylpyridines using a Brønsted-acidic ionic liquid as reusable catalyst. Monatshefte für Chemie — Chemical Monthly, 141, 867–870. DOI: 10.1007/s00706-010-0329-x.
Enyedy, I. J., Sakamuri, S., Zaman, W. A., Johnson, K. M., & Wang, S. M. (2003). Pharmacophore-based discovery of substituted pyridines as novel dopamine transporter inhibitors. Bioorganic & Medicinal Chemistry Letters, 13, 513–517. DOI: 10.1016/s0960-894x(02)00943-5.
Guo, J. J., Lou, H., Zhao, H., Wang, X. G., & Zheng, X. M. (2004). Novel synthesis of high surface area MgAl2O4 spinel as catalyst support. Materials Letters, 58, 1920–1923. DOI: 10.1016/j.matlet.2003.12.013.
Heravi, M. M., Bakhtiari, K., Daroogheha, Z., & Bamoharram, F. F. (2007). An efficient synthesis of 2,4,6-triarylpyridines catalyzed by heteropolyacid under solventfree conditions. Catalysis Communications, 8, 1991–1994. DOI: 10.1016/j.catcom.2007.03.028.
Khosropour, A. R., Mohammadpoor-Baltork, I., & Kiani, F. (2011). Green, new and efficient tandem oxidation and conversion of aryl alcohols to 2,4,6-triarylpyridines promoted by [HMIm]NO3-[BMIm]BF4 as a binary ionic liquid. Comptes Rendus Chimie, 14, 441–445. DOI: 10.1016/j.crci.2010.10.002.
Kim, B. Y., Ahn, J. B., Lee, H. W., Kang, S. K., Lee, J. H., Shin, J. S., Ahn, S. K., Hong, C. I., & Yoon, S. S. (2004). Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione. European Journal of Medicinal Chemistry, 39, 433–447. DOI: 10.1016/j.ejmech.2004.03.001.
Klimešová, V., Svoboda, M., Waisser, K., Pour, M., & Kaustová, J. (1999). New pyridine derivatives as potential antimicrobial agents. Il Farmaco, 54, 666–672. DOI: 10.1016/s0014-827x(99)00078-6.
Maleki, B., Azarifar, D., Veisi, H., Hojati, S. F., Salehabadi, H., & Nejat Yami, R. (2010). Wet 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient catalyst for the synthesis of 2,4,6-triarylpyridines under solvent-free conditions. Chinese Chemical Letters, 21, 1346–1349. DOI: 10.1016/j.cclet.2010.06.028.
Montazeri, N., & Mahjoob, S. (2012). Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate (PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions. Chinese Chemical Letters, 23, 419–422. DOI: 10.1016/j.cclet.2012.01.035.
Nagarapu, L., Aneesa, Peddiraju, R., & Apuri, S. (2007). HClO4-SiO2 as a novel and recyclable catalyst for the synthesis of 2,4,6-triarylpyridines under solvent-free conditions. Catalysis Communications, 8, 1973–1976. DOI: 10.1016/j.catcom.2007.08.003.
Navaei Alvar, E., Rezaei, M., & Navaei Alvar, H. (2010). Synthesis of mesoporous nanocrystalline MgAl2O4 spinel via surfactant assisted precipitation route. Powder Technology, 198, 275–278. DOI: 10.1016/j.powtec.2009.11.019.
Pillai, A. D., Rathod, P. D., Franklin, P. X., Patel, M., Nivsarkar, M., Vasu, K. K., Padh, H., & Sudarsanam, V. (2003). Novel drug designing approach for dual inhibitors as anti-inflammatory agents: implication of pyridine template. Biochemical and Biophysical Research Communications, 301, 183–186. DOI: 10.1016/s0006-291x(02)02996-0.
Safari, J., Khalili, S. D., Rezaei, M., Banitaba, S., & Meshkani, F. (2010). Nanocrystalline magnesium oxide: a novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives. Monatshefte für Chemie — Chemical Monthly, 141, 1339–1345. DOI: 10.1007/s00706-010-0397-y.
Safari, J., Banitaba, S. H., & Dehghan Khalili, S. (2011). Cobalt nanoparticles promoted highly efficient one pot fourcomponent synthesis of 1,4-dihydropyridines under solventfree conditions. Chinese Journal of Catalysis, 32, 1850–1855. DOI: 10.1016/s1872-2067(10)60295-1.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Safari, J., Zarnegar, Z. & Borujeni, M.B. Mesoporous nanocrystalline MgAl2O4: A new heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines under solvent-free conditions. Chem. Pap. 67, 688–695 (2013). https://doi.org/10.2478/s11696-013-0361-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-013-0361-5