European Journal of Chemistry

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

Article Sidebar

PDF
Published: Sep 30, 2012
DOI: https://doi.org/10.5155/eurjchem.3.3.310-313.659
Keywords:
Isatin, SBA-Pr-SO3H, Nano-reactor, Malononitrile, Knoevenagel condensation, 2-Oxoindolin-3-ylidene malononitrile
Section
Research Article
Issue
Vol. 3 No. 3 (2012): September 2012
Dates
Received 2012-07-02
Accepted 2012-07-12
Published 2012-09-30


Main Article Content

Negar Lashgari
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
Parisa Gholamzadeh
Department of Chemistry, Alzahra University, Vanak Square, 199389-1176, Tehran, Iran

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


icon graph This Abstract was viewed 3510 times | icon graph Article PDF downloaded 1112 times

How to Cite
(1)
Lashgari, N.; Ziarani, G. M.; 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, 310-313.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Research Council of Alzahra University and 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 © 2024 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).