European Journal of Chemistry 2012, 3(3), 279-282. doi:10.5155/eurjchem.3.3.279-282.630

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

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


Keywords


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

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DOI: 10.5155/eurjchem.3.3.279-282.630

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Citations

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[1]. 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
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[2]. 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
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[3]. 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
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[4]. 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
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[5]. 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
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[6]. 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
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[7]. 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
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[8]. Ghodsi Mohammadi Ziarani, Alireza Badiei, Monireh Shakiba Nahad, Malihe Hassanzadeh
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[9]. 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
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[10]. Mahshid Rahimifard, Ghodsi Mohammadi Ziarani, Alireza Badiei, Shima Asadi, Ali Abolhasani Soorki
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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. 21 Sep. 2019
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)

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

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