European Journal of Chemistry 2012, 3(3), 310-313. doi:10.5155/eurjchem.3.3.310-313.659

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

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


Keywords


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

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DOI: 10.5155/eurjchem.3.3.310-313.659

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Citations

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[1]. GHODSI MOHAMMADI ZIARANI, SOMAYEH MOUSAVI, NEGAR LASHGARI, ALIREZA BADIEI
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[2]. Ghodsi Mohammadi Ziarani, Nina Hosseini Mohtasham, Negar Lashgari, Alireza Badiei
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[3]. Ghodsi Mohammadi Ziarani, Alireza Badiei, Monireh Shakiba Nahad, Malihe Hassanzadeh
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[4]. Ghodsi Mohammadi Ziarani, Zhila Kazemi Asl, Parisa Gholamzadeh, Alireza Badiei, Morteza Afshar
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[5]. Naveen Gupta, Tamal Roy, Debashis Ghosh, Sayed H. R. Abdi, Rukhsana I. Kureshy, Noor-ul H. Khan, Hari C. Bajaj
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[6]. Mahshid Rahimifard, Ghodsi Mohammadi Ziarani, Alireza Badiei, Shima Asadi, Ali Abolhasani Soorki
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[7]. Luyi Zhu, Peipei Yan, Lvye Zhang, Zhangtao Chen, Xiaofei Zeng, Guofu Zhong
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[8]. Parisa Gholamzadeh, Ghodsi Mohammadi Ziarani, Alireza Badiei, Zohreh Bahrami
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[9]. Parisa Gholamzadeh, Ghodsi Mohammadi Ziarani, Alireza Badiei, Ali Abolhassani Soorki, Negar Lashgari
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[10]. Ghodsi Mohammadi Ziarani, Negar Lashgari, Alireza Badiei
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[11]. Rajesh H. Vekariya, Hitesh D. Patel
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[12]. Ghodsi Mohammadi Ziarani, Zhila Kazemi Asl, Parisa Gholamzadeh, Alireza Badiei, Morteza Afshar
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DOI: 10.1007/s10971-017-4522-9
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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. 22 Jan. 2019
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)

DOI Link: https://doi.org/10.5155/eurjchem.3.3.310-313.659

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