European Journal of Chemistry 2012, 3(3), 310-313 | doi: https://doi.org/10.5155/eurjchem.3.3.310-313.659 | Get rights and content

Issue cover





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

Knoevenagel condensation of isatins with malononitrile/ethyl cyanoacetate in the presence of sulfonic acid functionalized silica (SBA-Pr-SO3H) as a new nano-reactor


Negar Lashgari (1) , Ghodsi Mohammadi Ziarani (2,*) , Alireza Badiei (3) , Parisa Gholamzadeh (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) Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran
(*) Corresponding Author

Received: 02 Jul 2012 | Accepted: 12 Jul 2012 | Published: 30 Sep 2012 | Issue Date: September 2012

Abstract


The Knoevenagel condensation between isatins and active methylene compounds like malononitrile and ethyl cyanoacetate to prepare 2-oxoindolin-3-ylidene malononitrile/ cyanoacetates is described. The reactions occur in the presence of sulfonic acid functionalized silica SBA-15 (SBA-Pr-SO3H) in an aqueous medium giving excellent yields of the products in short reaction times. SBA-Pr-SO3H with a pore size of 6 nm is found to be an efficient and environmentally benign catalyst for this reaction.

3_3_310_313_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


Isatin; SBA-Pr-SO3H; Nano-reactor; Malononitrile; Knoevenagel condensation; 2-Oxoindolin-3-ylidene malononitrile

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.3.3.310-313.659

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 3150 times | icon graph PDF Article downloaded 939 times

Funding information


Research Council of Alzahra University and University of Tehran, Iran

Citations

/


[1]. Shaimaa Sindi, Nizar El Guesmi, Basim H. Asghar, Essam M. Hussein
Structure-reactivity relationships on Michael additions of secondary cyclic amines with 3-cyanomethylidene-2-oxindoline derivatives
Arabian Journal of Chemistry  13(5), 5487, 2020
DOI: 10.1016/j.arabjc.2020.03.027
/


[2]. Behnam Gholipour, Salman Shojaei, Sadegh Rostamnia, Mohammad Reza Naimi-Jamal, Dokyoon Kim, Taras Kavetskyy, Nasrin Nouruzi, Ho Won Jang, Rajender S. Varma, Mohammadreza Shokouhimehr
Metal-free nanostructured catalysts: sustainable driving forces for organic transformations
Green Chemistry  23(17), 6223, 2021
DOI: 10.1039/D1GC01366A
/


[3]. Ghodsi Mohammadi Ziarani, Zhila Kazemi Asl, Parisa Gholamzadeh, Alireza Badiei, Morteza Afshar
The use of SrFe12O19 magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction
Applied Organometallic Chemistry  31(12), , 2017
DOI: 10.1002/aoc.3830
/


[4]. Naveen Gupta, Tamal Roy, Debashis Ghosh, Sayed H. R. Abdi, Rukhsana I. Kureshy, Noor-ul H. Khan, Hari C. Bajaj
Ordered short channel mesoporous silica modified with 1,3,5-triazine–piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
RSC Advances  5(23), 17843, 2015
DOI: 10.1039/C5RA00406C
/


[5]. 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
/


[6]. João Marcos Gomes de Oliveira Ferreira, Girlyanderson Araújo da Silva, Maísa Cavalcanti Coelho, Claudio Gabriel Lima Junior, Juliana Alves Vale
Quick synthesis of isatin-derived knoevenagel adducts using only eco-friendly solvent
Results in Chemistry  3, 100135, 2021
DOI: 10.1016/j.rechem.2021.100135
/


[7]. 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
/


[8]. 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
/


[9]. Ghodsi Mohammadi Ziarani, Zhila Kazemi Asl, Parisa Gholamzadeh, Alireza Badiei, Morteza Afshar
Sol–gel auto-combustion production of SrFe12O19 magnetic nanoparticles and its application in the synthesis of spirooxindol–quinazolinone derivatives
Journal of Sol-Gel Science and Technology  85(1), 103, 2018
DOI: 10.1007/s10971-017-4522-9
/


[10]. GHODSI MOHAMMADI ZIARANI, SOMAYEH MOUSAVI, NEGAR LASHGARI, ALIREZA BADIEI
Mesostructured SBA-15-Pr-SO3H: An efficient solid acid catalyst for one-pot and solvent-free synthesis of 3,4-dihydro-2-pyridone derivatives
Journal of Chemical Sciences  125(6), 1359, 2013
DOI: 10.1007/s12039-013-0511-x
/


[11]. Ghodsi Mohammadi Ziarani, Nina Hosseini Mohtasham, Negar Lashgari, Alireza Badiei
Efficient one-pot synthesis of 2H-indazolo[2,1-b]phthalazinetrione derivatives with amino-functionalized nanoporous silica (SBA-Pr-NH2) as catalyst
Research on Chemical Intermediates  41(10), 7581, 2015
DOI: 10.1007/s11164-014-1845-9
/


[12]. Aliyeh Feghhi, Reihaneh Malakooti, Sadeq Malakooti, Nasrin Hooshmand
Easy Scale‐Up Synthesis of Mo8O26(C5H6N)4.H2O Hybrid with a Rectangular Prism Morphology and Its Application as an Efficient and Highly Recyclable Bi‐functional Catalyst for Knoevenagel Condensations
ChemistrySelect  4(9), 2551, 2019
DOI: 10.1002/slct.201803124
/


[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]. Luyi Zhu, Peipei Yan, Lvye Zhang, Zhangtao Chen, Xiaofei Zeng, Guofu Zhong
TiCl4/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds
RSC Advances  7(81), 51352, 2017
DOI: 10.1039/C7RA09951G
/


[15]. Parisa Gholamzadeh, 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  3(3), 279, 2012
DOI: 10.5155/eurjchem.3.3.279-282.630
/


[16]. 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
/


References


[1]. Tietze, L. F.; Beifuss, U. Comprehensive Organic Synthesis, Pergamon Press: Oxford, 1991.

[2]. DaSilva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273-324.
http://dx.doi.org/10.1590/S0103-50532001000300002

[3]. Lashgari, N.; Mohammadi Ziarani, G. Arkivoc 2012, 1, 277-320.

[4]. Chakrabarty, M.; Mukherjee, R.; Arima, S.; Harigaya, Y. Heterocycles 2009, 78, 139-149.
http://dx.doi.org/10.3987/COM-08-11504

[5]. Jursic, B. S.; Stevens, E. D. Tetrahedron Lett. 2002, 43, 5681-5683.
http://dx.doi.org/10.1016/S0040-4039(02)01107-3

[6]. Safer, A.; Rahmouni, M.; Carreaux, F.; Paquin, L.; Lozach, O.; Meijer, L.; Bazureau, J. P. Chem. Pap. 2011, 65, 332-337.
http://dx.doi.org/10.2478/s11696-010-0104-9

[7]. Abass, M.; Mohamed, E. A.; Ismail, M. M.; Mayas, A. S. Eur. J. Chem. 2011, 2, 278-287.
http://dx.doi.org/10.5155/eurjchem.2.3.378-387.351

[8]. 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

[9]. Inoue, S.; Okada, K.; Tanino, H.; Hashizume, K.; Kakoi, H. Tetrahedron 1994, 50, 2729-2752.
http://dx.doi.org/10.1016/S0040-4020(01)86989-1

[10]. Inoue, S.; Okada, K.; Tanino, H.; Kakoi, H. Tetrahedron Lett. 1986, 27, 5225-5228.
http://dx.doi.org/10.1016/S0040-4039(00)85175-8

[11]. Freeman, F. Chem. Rev. 1969, 69, 591-624.
http://dx.doi.org/10.1021/cr60261a001
PMid:4897955

[12]. Harley-Mason, J.; Ingleby, R. F. J. J. Chem. Soc. 1958, 3639-3642.
http://dx.doi.org/10.1039/jr9580003639

[13]. Junek, H.; Dworczak, R.; Sterk, H.; Fabian, W. Liebigs Ann. Chem. 1989, 1989, 1065-1069.

[14]. Capuano, L.; Diehl, V.; Ebner, W. Chem. Ber. 1972, 105, 3407-3412.
http://dx.doi.org/10.1002/cber.19721051028

[15]. Katritzky, A. R.; Fan, W. Q.; Liang, D. S.; Li, Q. L. J. Heterocycl. Chem. 1989, 26, 1541-1545.
http://dx.doi.org/10.1002/jhet.5570260607

[16]. Dandia, A.; Taneja, H.; Gupta, R.; Paul, S. Synth. Commun. 1999, 29, 2323-2335.
http://dx.doi.org/10.1080/00397919908086235

[17]. Sachdeva, H.; Dandia, A.; Singh, H. L. Org. Chem. Indian J. 2008, 4, 508-512.

[18]. Dandia, A.; Singh, R.; Sarawgi, S.; Khaturia, S. Chin. J. Chem. 2006, 24, 950-954.
http://dx.doi.org/10.1002/cjoc.200690180

[19]. Demchuk, D. V.; Elinson, M. N.; Nikishin, G. I. Mendelev Commun. 2011, 21, 224-225.
http://dx.doi.org/10.1016/j.mencom.2011.07.018

[20]. Wight, A. P.; Davis, M. E. Chem. Rev. 2002, 102, 3589-3614.
http://dx.doi.org/10.1021/cr010334m
PMid:12371895

[21]. Lim, M. H.; Blanford, C. F.; Stein, A. Chem. Mater. 1998, 10, 467-470.
http://dx.doi.org/10.1021/cm970713p

[22]. Naik, M. A.; Sachdev, D.; Dubey, A. Catal. Commun. 2010, 11, 1148-1153.
http://dx.doi.org/10.1016/j.catcom.2010.06.004

[23]. Karimi, B.; Vafaeezadeh, M. Chem. Commun. 2012, 48, 3327-3329.
http://dx.doi.org/10.1039/c2cc17702a
PMid:22361844

[24]. VanGrieken, R.; Melero, J. A.; Morales, G. Appl. Catal. A 2005, 289, 143-152.
http://dx.doi.org/10.1016/j.apcata.2005.04.059

[25]. Li, C.; Yang, J.; Wang, P.; Liu, J.; Yang, Q. Micropor. Mesopor. Mater. 2009, 123, 228-233.
http://dx.doi.org/10.1016/j.micromeso.2009.04.005

[26]. Ziarani, G. M.; Badiei, A.; Shahjafari, F.; Pourjafar, T. S. Afr. J. Chem. 2012, 65, 10-13.

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

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

[29]. Ziarani, G. M.; Badiei, A. R.; Azizi, M. Sci. Iran. 2011, 18, 453-457.
http://dx.doi.org/10.1016/j.scient.2011.05.008

[30]. Gholamzadeh, P; Ziarani, G. M.; Badiei, A.; Bahrami, Z. Eur. J. Chem. 2012, 3(3), 279-282.
http://dx.doi.org/10.5155/eurjchem.3.3.279-282.630

[31]. Jones, G.; Rae, W. J. Tetrahedron 1966, 22, 3021-3026.
http://dx.doi.org/10.1016/S0040-4020(01)82281-X

[32]. Dandia, A.; Arya, K.; Sati, M.; Sharma, R. Heterocycl. Commun. 2003, 9, 415-420.
http://dx.doi.org/10.1515/HC.2003.9.4.415

[33]. Redkin, R. G.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Tetrahedron 2007, 63, 11444-11450.
http://dx.doi.org/10.1016/j.tet.2007.08.050

[34]. Shemchuk, L. A.; Chernykh, V. P.; Redkin, R. G. Russ. J. Org. Chem. 2008, 44, 1789-1794.
http://dx.doi.org/10.1134/S1070428008120117

[35]. Abdelhamid, I. A.; Mohamed, M. H.; Abdelmoniem, A. M.; Ghozlan, S. A. S. Tetrahedron 2009, 65, 10069-10073.
http://dx.doi.org/10.1016/j.tet.2009.09.081


How to cite


Lashgari, N.; Ziarani, G.; Badiei, A.; Gholamzadeh, P. Eur. J. Chem. 2012, 3(3), 310-313. doi:10.5155/eurjchem.3.3.310-313.659
Lashgari, N.; Ziarani, G.; Badiei, A.; Gholamzadeh, P. Knoevenagel condensation of isatins with malononitrile/ethyl cyanoacetate in the presence of sulfonic acid functionalized silica (SBA-Pr-SO3H) as a new nano-reactor. Eur. J. Chem. 2012, 3(3), 310-313. doi:10.5155/eurjchem.3.3.310-313.659
Lashgari, N., Ziarani, G., Badiei, A., & Gholamzadeh, P. (2012). 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), 310-313. doi:10.5155/eurjchem.3.3.310-313.659
Lashgari, Negar, 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 [Online], 3.3 (2012): 310-313. Web. 30 Nov. 2023
Lashgari, Negar, Ziarani, Ghodsi, Badiei, Alireza, AND Gholamzadeh, Parisa. "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 [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.3.3.310-313.659


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), 310-313 | doi: https://doi.org/10.5155/eurjchem.3.3.310-313.659 | 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.