European Journal of Chemistry 2012, 3(3), 279-282 | doi: https://doi.org/10.5155/eurjchem.3.3.279-282.630 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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) , Ghodsi Mohammadi Ziarani (2,*) , Alireza Badiei (3) , Zohreh Bahrami (4)

(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.

3_3_279_282_800


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


Oxindole; SBA-Pr-SO3H; Green synthesis; Solvent free reaction; Tyrosin kinase inhibitor; Arylidene-1,3-dihydroindole-2-ones

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.3.3.279-282.630

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2653 times | icon graph PDF Article downloaded 759 times

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
Organic & Biomolecular Chemistry  18(40), 8058, 2020
DOI: 10.1039/D0OB01571G
/


[10]. Dnyaneshwar Sanap, Lata Avhad, Suresh Ghotekar, Nitin D. Gaikwad
An expedient synthesis of C3-arylidene-oxindole derivatives using calcite nanoflowers as an efficient heterogeneous catalyst
Inorganic Chemistry Communications  149, 110387, 2023
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
European Journal of Chemistry  3(3), 310, 2012
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


How to cite


Gholamzadeh, P.; Ziarani, G.; Badiei, A.; Bahrami, Z. Eur. J. Chem. 2012, 3(3), 279-282. doi:10.5155/eurjchem.3.3.279-282.630
Gholamzadeh, P.; Ziarani, G.; 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(3), 279-282. doi:10.5155/eurjchem.3.3.279-282.630
Gholamzadeh, P., Ziarani, G., Badiei, A., & Bahrami, Z. (2012). Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the solvent free synthesis of (E)-arylidene-1,3-dihydroindole-2-ones. European Journal of Chemistry, 3(3), 279-282. doi:10.5155/eurjchem.3.3.279-282.630
Gholamzadeh, Parisa, Ghodsi Mohammadi Ziarani, Alireza Badiei, & Zohreh Bahrami. "Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the solvent free synthesis of (E)-arylidene-1,3-dihydroindole-2-ones." European Journal of Chemistry [Online], 3.3 (2012): 279-282. Web. 30 Sep. 2023
Gholamzadeh, Parisa, Ziarani, Ghodsi, Badiei, Alireza, AND Bahrami, Zohreh. "Application of sulfonic acid functionalized nanoporous silica (SBA-Pr-SO3H) in the solvent free synthesis of (E)-arylidene-1,3-dihydroindole-2-ones" European Journal of Chemistry [Online], Volume 3 Number 3 (30 September 2012)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.3.3.279-282.630


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2012, 3(3), 279-282 | doi: https://doi.org/10.5155/eurjchem.3.3.279-282.630 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.