

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




(1) Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran
(2) Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran
(3) School of Chemistry, College of Science, University of Tehran, 14155-6455, Tehran, Iran
(4) School of Chemistry, College of Science, University of Tehran, 14155-6455, Tehran, Iran
(*) Corresponding Author
Received: 05 May 2012 | Accepted: 02 Jun 2012 | Published: 30 Sep 2012 | Issue Date: September 2012
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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European Journal of Chemistry
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DOI: 10.5155/eurjchem.3.3.279-282.630
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Funding information
Research Council of Alzahra University and the University of Tehran, Iran
Citations
[1]. Ghodsi Mohammadi Ziarani, Sakineh Faramarzi, Negar Lashgari, Alireza Badiei
A simple and clean method for multicomponent synthesis of spiro [indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions
Journal of the Iranian Chemical Society 11(3), 701, 2014
DOI: 10.1007/s13738-013-0342-1

[2]. Ghodsi Mohammadi Ziarani, Negar Lashgari, Alireza Badiei
Sulfonic acid-functionalized mesoporous silica (SBA-Pr-SO3H) as solid acid catalyst in organic reactions
Journal of Molecular Catalysis A: Chemical 397, 166, 2015
DOI: 10.1016/j.molcata.2014.10.009

[3]. Vaezeh Fathi Vavsari, Ghodsi Mohammadi Ziarani, Alireza Badiei, Saeed Balalaie
Application of SBA-Pr-SO3H as a nanoreactor in the one-pot synthesis of spiroquinazolinones
Journal of the Iranian Chemical Society 13(6), 1037, 2016
DOI: 10.1007/s13738-016-0817-y

[4]. Rajesh H. Vekariya, Hitesh D. Patel
Sulfonic Acid–Functionalized Silica (SiO2-Pr-SO3H) as a Solid and a Heterogeneous Catalyst in Green Organic Synthesis: Recent Advances
Synthetic Communications 45(9), 1031, 2015
DOI: 10.1080/00397911.2014.997364

[5]. Md. Nurnobi Rashed, Abeda Sultana Touchy, Chandan Chaudhari, Jaewan Jeon, S.M.A. Hakim Siddiki, Takashi Toyao, Ken-ichi Shimizu
Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst
Chinese Journal of Catalysis 41(6), 970, 2020
DOI: 10.1016/S1872-2067(19)63515-1

[6]. Mahshid Rahimifard, Ghodsi Mohammadi Ziarani, Alireza Badiei, Shima Asadi, Ali Abolhasani Soorki
One-pot solvent-free synthesis of 1,8-dioxo-octahydroxanthene derivatives using sulfonic acid-functionalized LUS-1 and their antimicrobial activities
Research on Chemical Intermediates 42(4), 3847, 2016
DOI: 10.1007/s11164-015-2248-2

[7]. Kovuru Gopalaiah, Ankit Tiwari
Synthesis of (E)‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines
European Journal of Organic Chemistry 2020(46), 7229, 2020
DOI: 10.1002/ejoc.202001300

[8]. Parisa Gholamzadeh, Ghodsi Mohammadi Ziarani, Alireza Badiei, Ali Abolhassani Soorki, Negar Lashgari
Efficient green synthesis of isoindigo derivatives using sulfonic-acid-functionalized nanoporous silica (SBA-Pr-SO3H) catalyst and study of their antimicrobial properties
Research on Chemical Intermediates 39(9), 3925, 2013
DOI: 10.1007/s11164-012-0909-y

[9]. Nuria Martín, Francisco G. Cirujano
Organic synthesis of high added value molecules with MOF catalysts
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DOI: 10.1039/D0OB01571G

[10]. Dnyaneshwar Sanap, Lata Avhad, Suresh Ghotekar, Nitin D. Gaikwad
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DOI: 10.1016/j.inoche.2022.110387

[11]. Negar Lashgari, Ghodsi Mohammadi Ziarani, Alireza Badiei, Parisa Gholamzadeh
Knoevenagel condensation of isatins with malononitrile/ethyl cyanoacetate in the presence of sulfonic acid functionalized silica (SBA-Pr-SO3H) as a new nano-reactor
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DOI: 10.5155/eurjchem.3.3.310-313.659

[12]. Ghodsi Mohammadi Ziarani, Leila Seyedakbari, Shima Asadi, Alireza Badiei, Marzieeh Yadavi
Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives
Research on Chemical Intermediates 42(2), 499, 2016
DOI: 10.1007/s11164-015-2036-z

[13]. Ghodsi Mohammadi Ziarani, Alireza Badiei, Monireh Shakiba Nahad, Malihe Hassanzadeh
Application of SBA-Pr-SO3H in the synthesis of benzoxazole derivatives
European Journal of Chemistry 3(4), 433, 2012
DOI: 10.5155/eurjchem.3.4.433-436.673

[14]. Limin Zang, Jianhui Qiu, Chao Yang, Eiichi Sakai
Preparation and Characterization of Bayberry-Like Polypyrrole Composites Using Functionalized Mesoporous Silica asIn SituDopant
International Journal of Polymeric Materials and Polymeric Biomaterials 64(9), 489, 2015
DOI: 10.1080/00914037.2014.977896

[15]. Madiha M. Siddiqui, Amol A. Nagargoje, Akram K. Raza, Parshuram M. Pisal, Bapurao B. Shingate
[Et3NH][HSO4] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives
Journal of Heterocyclic Chemistry 59(5), 899, 2022
DOI: 10.1002/jhet.4429

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
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