Abstract
This study is aimed at proposing a practical green procedure for the synthesis of octahydroquinazolinone derivatives using benzaldehyde, dimedone and urea under microwave irradiation in water. A surfactant type polyoxometalate-based organic–inorganic hybrid was able to efficiently catalyze this synthesis. The catalyst was prepared and characterized by Fourier transform infrared, UV–Vis, X-ray diffraction, and thermogravimetric analysis. The employed catalyst exerted a synergistic effect; the anion part acted as a catalyst while the cation part acted as a surfactant in order to increase the concentration of organic reactants in water. The main advantage of this method is its remarkable yield in short reaction periods, which results in the rendering of products with high purity. Moreover, this heterocatalyst is capable of being easily recovered and reused several times. The influences of reaction conditions were studied systematically, and a possible catalysis mechanism was proposed for understanding the highly efficient heterogeneous catalytic behavior.
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M. Kidwai, S. Sexena, M. K. R. Khan, and S. S. Thural (2005). Eur. J. Med. Chem. doi:10.1016/j.ejmech.2005.02.009.
J. S. Wilkes (2002). Green Chem. doi:10.1039/b110838g.
M. Ashok, B. S. Holla, and N. Kumari (2007). Eur. J. Med. Chem. doi:10.1016/j.ejmech.2006.09.003.
G. C. Rovnyak, K. S. Atwal, A. Hedberg, S. D. Kimball, S. Moreland, J. Z. Gougoutas, B. C. O’Reilly, J. Schwartz, and M. F. Malley (1992). J. Med. Chem. doi:10.1021/jm00095a023.
M. Yarim, S. Sarac, M. Ertan, S. F. Kilic, and K. Erol (2002). Arzneimittelforschung. doi:10.1055/s-0031-1299852.
K. S. Atwal, G. C. Rovnyak, B. C. O. Reilly, and J. Schwartz (1989). J. Org. Chem. doi:10.1021/jo00286a020.
M. Yarim, S. Sarac, S. F. Kilic, and K. Erol (2003). II Farmaco. doi:10.1016/S0014-827X(02)00009-5.
C. O. Kappe, W. M. F. Fabian, and M. A. Semones (1997). Tetrahedron. doi:10.1016/s0040-4020(97)00022-7.
K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, and B. C. O’Reilly (1991). J. Med. Chem. doi:10.1021/jm00106a048.
S. P. Maradur and G. S. Gokavi (2007). Catal. Commun. doi:10.1016/j.catcom.2006.05.048.
M. Kidwani, M. Venkatramanan, and K. R. Bhushan (2000). J. Chem. Res. doi:10.3184/030823400103166292.
R. Sheldon (2001). Chem. comm. doi:10.1039/b107270f.
K. Gong, Z. W. He, Y. Xu, D. Fang, and Z. L. Liu (2008). Monatsh. Chem. doi:10.1007/s00706-008-0871-y.
T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, and T. J. Mitchison (1999). Science. doi:10.1126/science.286.5441.971.
Z. Hassani, M. R. Islami, and M. Kalantari (2006). Bioorg. Med. Chem. Lett. doi:10.1016/j.bmcl.2006.06.038.
S. K. De and R. A. Gibbs (2005). Synthesis. doi:10.1055/s-2005-869899.
G. Sabitha, G. S. K. Reddy, and J. S. Yadav (2003). Tetrahedron Lett. doi:10.1016/s0040-4039(03)01564-8.
J. S. Yadav, B. V. Subba Reddy, R. Sriniva, C. Venugopal, and T. Ramalingam (2001). Synthesis. doi:10.1055/s-2001-15229.
C. Jiang and D. Y. Qi (2007). Chin. Chem. Lett. doi:10.1016/j.cclet.2007.04.002.
Y. Yu, D. Liu, C. Liu, and G. Lu (2007). Bioorg. Med. Chem. Lett. doi:10.1016/j.bmcl.2006.12.068.
S. Tu, F. Fang, S. Zhu, T. Li, X. Zhang, and Q. Zhuang (2004). Synlett. doi:10.1055/s-2004-815419.
P. Salehi, M. Dabiri, M. A. Zolfigol, and M. B. A. Fard (2003). Tetrahedron Lett. doi:10.1016/s0040-4039(03)00436-2.
Z. L. Shen, W. J. Zhou, Y. T. Liu, S. J. Ji, and T. P. Loh (2008). Green Chem. doi:10.1039/b717235d.
J. J. Peng and Y. Q. Deng (2001). Tetrahedron Lett. doi:10.1016/s0040-4039(00)01974-2.
P. Wasserscheid and W. Keim (2000). Angew. Chem. doi:10.1002/1521-3773(20001103)39:21<3772:aid-anie3772>3.0.co;2-5.
K. Niralwad, B. Shingate, and M. Shingare (2010). J. Chin. Chem. Soc. doi:10.1002/jccs.201000014.
H. M. Hügel (2009). Molecules. doi:10.3390/molecules14124936.
R. Rajagopal, D. V. Jarikote, and K. V. Srinivasan (2002). Chem. Commun. doi:10.1039/b111271f.
A. Gaplovsky, M. Goplosky, S. Toma, and J. L. Luche (2000). J. Org. Chem. doi:10.1021/jo000611+.
T. Welton (1999). Chem. Rev. doi:10.1021/cr980032t.
N. N. Tonkikh, A. Strakovs, and M. V. Petrova (2004). Chem. Heterocycl. Compd. doi:10.1023/b:cohc.0000023766.76924.78.
C. Brevard, R. Schimpf, G. Tourne, et al. (1983). J. Am. Chem. Soc. doi:10.1021/ja00362a008.
M. M. Heravi, F. Derikvand, and F. Bomoharram (2005). J. Mol. Catal. A Chem. doi:10.1016/j.molcata.2005.08.009.
X. Zhao, J. Yan, X. Xue, Zh Han, Sh Cui, L. Zong, L. Zheng, Ch Shen, H. Yu, and X. Zhai (2014). Inorg. Chim. Acta. doi:10.1016/j.ica.2014.01.033.
W. G. Klemperer and R. K. C. Ho (1978). J. Am. Chem. Soc. doi:10.1021/ja00489a048.
S. Lin, X. Zhang, and M. Luo (2009). J. Solid State Eelectr. doi:10.1007/s10008-008-0735-8.
B. Karimi and D. Zareyee (2008). Org. Lett. doi:10.1021/ol8013107.
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The authors gratefully acknowledge financial support of this research by Shahid Chamran (Ahvaz) University.
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Mozafari, R., Heidarizadeh, F. One Pot Synthesis of Octahydroquinazolinone Derivatives Using (Me (Im)12) H4CuPW11O39 as a Surfactant Type Catalyst. J Clust Sci 27, 1629–1643 (2016). https://doi.org/10.1007/s10876-016-1023-x
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DOI: https://doi.org/10.1007/s10876-016-1023-x