European Journal of Chemistry

Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the solvent free synthesis of (E)-arylidene-1,3-dihydroindole-2-ones



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Parisa Gholamzadeh
Ghodsi Mohammadi Ziarani
Alireza Badiei
Zohreh Bahrami

Abstract

An efficient and green condensation reaction is developed for the synthesis of (E)-arylidene-1,3-dihydroindole-2-ones; (1), using heterogeneous nanoporous acid catalyst of SBA-Pr-SO3H with pore size, 6 nm in solvent free condition. Arylidene-1,3-dihydroindole-2-ones have many pharmaceutical properties such as Tyrosin kinase inhibiton. This method has the advantages of short reaction time, isolation ease of the products, excellent yields and recyclable catalyst.

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Gholamzadeh, P.; Ziarani, G. M.; Badiei, A.; Bahrami, Z. Application of Sulfonic Acid Functionalized Nanoporous Silica (SBA-Pr-SO3H) in the Solvent Free Synthesis of (E)-Arylidene-1,3-Dihydroindole-2-Ones. Eur. J. Chem. 2012, 3, 279-282.

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References

[1]. Zhao, D.; Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Science 1998, 279, 548-552.
http://dx.doi.org/10.1126/science.279.5350.548
PMid:9438845

[2]. Zhao, D.; Huo, Q.; Feng, J.; Chmelka, B. F.; Stucky, G. D. J. Am. Chem. Soc. 1998, 120, 6024-6036.
http://dx.doi.org/10.1021/ja974025i

[3]. Hajiaghababaei, L.; Badiei, A.; Ganjali, M. R.; Heydari, S.; Khaniani, Y.; Ziarani, G. M. Desalination 2011, 266, 182-187.
http://dx.doi.org/10.1016/j.desal.2010.08.024

[4]. Liu, Q.; Wang, A.; Wang, X.; Zhang, T. Chem. Mater. 2006, 18, 5153-5155
http://dx.doi.org/10.1021/cm0615727

[5]. Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Nature 1992, 359, 710-712.
http://dx.doi.org/10.1038/359710a0

[6]. Bahrami, K.; Khodaei, M. M.; Fattahpour, P. Catal. Sci. Technol. 2011, 1, 389-393.
http://dx.doi.org/10.1039/c1cy00053e

[7]. Grieken, R. V.; Melero, J. A.; Morales, G. J. Mol. Catal. A: Chem. 2006, 256, 29-36.
http://dx.doi.org/10.1016/j.molcata.2006.04.040

[8]. Margolese, D.; Melero, J. A.; Christiansen, S. C.; Chmelka, B. F.; Stucky, G. D. Chem. Mater. 2000, 12, 2448-2459.
http://dx.doi.org/10.1021/cm0010304

[9]. Ziarani, G. M.; Badiei, A.; Aslani, Z.; Lashgari, N. Arabian J. Chem. 2012, In Press.

[10]. Ziarani, G. M.; Badiei, A.; Khaniania, Y.; Haddadpour, M. Iran. J. Chem. Chem. Eng. 2010, 29, 1-10.

[11]. Ziarani, G. M.; Badiei, A.; Haddadpour, M. Int. J. Chem. 2011, 3, 87-94.

[12]. Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. J. Med. Chem. 1998, 41, 2588-2603.
http://dx.doi.org/10.1021/jm980123i
PMid:9651163

[13]. Wood, E. R.; Kuyper, L.; Petrov, K. G.; Hunter, R. N.; Harris, P. A.; Lackey, K. Bioorg. Med. Chem. Lett. 2004, 14, 953-958.
http://dx.doi.org/10.1016/j.bmcl.2003.12.002

[14]. Ölgen, S.; Akaho, E.; Nebioglu, D. II Farmaco 2005, 60, 497-506.
http://dx.doi.org/10.1016/j.farmac.2005.01.015
PMid:15927182

[15]. Spencer, J.; Chowdhry, B. Z.; Hamid, S.; Mendham, A. P.; Male, L.; Coles, S. J.; Hursthouse, M. B. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2010, 66, o71-o78.
http://dx.doi.org/10.1107/S0108270109054134
PMid:20124685

[16]. Ölgen, S.; Göze, C.; Jose, J. Biol. Pharm. Bull. 2007, 30, 715-718.

[17]. Cheng, J. B.; Cooper, K.; Duplantier, A. J.; Eggler, J. F.; Kraus, K. G.; Marshall, S. C.; Marfat, A.; Masamune, H.; Shirley, J. T.; Tickner, J. E.; Umland, J. P. Bioorg. Med. Chem. Lett. 1995, 5, 1969-1972.
http://dx.doi.org/10.1016/0960-894X(95)00334-P

[18]. Robinson, R. P.; Reiter, L. A.; Barth, W. E.; Campeta, A. M.; Cooper, K.; Cronin, B. J.; Destito, R.; Donahue, K. M.; Falkner, F. C.; Fiese, E. F.; Johnson, D. L.; Kuperman, A. V.; Liston, T. E.; Malloy, D.; Martin, J. J.; Mitchell, D. Y.; Rusek, F. W.; Shamblin, S. L.; Wright, C. F. J. Med. Chem. 1996, 39, 10-18.
http://dx.doi.org/10.1021/jm950575k
PMid:8568796

[19]. Woodard, C. L.; Li, Z.; Kathcart, A. K.; Terrell, J.; Gerena, L.; Lopez-Sanchez, M.; Kyle, D. E.; Bhattacharjee, A. K.; Nichols, D. A.; Ellis, W.; Prigge, S. T.; Geyer, J. A.; Waters, N. C. J. Med. Chem. 2003, 46, 3877-3882.
http://dx.doi.org/10.1021/jm0300983
PMid:12930149

[20]. Villemin, D.; Martin, B. Synth. Commun. 1998, 28, 3201-3208.
http://dx.doi.org/10.1080/00397919808004422

[21]. Hu, Y.; Kang, H.; Zeng, B. W.; Wei, P.; Huang, H. J. Chem. Res. 2008, 2008, 642-643.

[22]. Zhang, W.; Go, M. L. Bioorg. Med. Chem. 2009, 17, 2077-2090.
http://dx.doi.org/10.1016/j.bmc.2008.12.052

[23]. Pandit, B.; Sun, Y.; Chen, P.; Sackett, D. L.; Hu, Z.; Rich, W.; Li, C.; Lewis, A.; Schaefera, K.; Li, P. K. Bioorg. Med. Chem. 2006, 14, 6492-6501.
http://dx.doi.org/10.1016/j.bmc.2006.06.017

[24]. Walker, G. N.; Smith, R. T.; Weaver, B. N. J. Med. Chem. 1965, 8, 626-637.
http://dx.doi.org/10.1021/jm00329a016

[25]. Xu, T. T.; Wang, S. Y.; Ji, S. J. Chin. J. Org. Chem. 2006, 26, 1414-1417.

[26]. Chatten, L. G.; Daisley, R. W.; Olliff, C. J. J. Chem. Soc., Perkin Trans. 2 1973, 469-473.
http://dx.doi.org/10.1039/p29730000469

[27]. Kniess, T.; Bergmann, R.; Kuchar, M.; Steinbach, J.; Wuest, F. Bioorg. Med. Chem. Lett. 2009, 17, 7732-7742.
http://dx.doi.org/10.1016/j.bmc.2009.09.038

[28]. Lashgari, N.; Ziarani, G. M.; Badiei, A.; Gholamzadeh, P. Eur. J. Chem. 2012, 3(3), 310-313.
http://dx.doi.org/10.5155/eurjchem.3.3.310-313.659

Supporting Agencies

Research Council of Alzahra University and the University of Tehran, Iran
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