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

Article Sidebar

PDF
Published: Sep 30, 2012
DOI: https://doi.org/10.5155/eurjchem.3.3.279-282.630
Keywords:
Oxindole, SBA-Pr-SO3H, Green synthesis, Solvent free reaction, Tyrosin kinase inhibitor, Arylidene-1, 3-dihydroindole-2-ones
Section
Research Article
Issue
Vol. 3 No. 3 (2012): September 2012
Dates
Received 2012-05-05
Accepted 2012-06-02
Published 2012-09-30


Main Article Content

Parisa Gholamzadeh
Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran
Ghodsi Mohammadi Ziarani
Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran
Alireza Badiei
School of Chemistry, College of Science, University of Tehran, 14155-6455, Tehran, Iran
Zohreh Bahrami
School of Chemistry, College of Science, University of Tehran, 14155-6455, Tehran, Iran

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.

3_3_279_282_800


icon graph This Abstract was viewed 3370 times | icon graph Article PDF downloaded 1068 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).