Generic placeholder image

Letters in Organic Chemistry

Author(s): Fatemeh Hakimi, Iman Salimi and Mehdi Fallah-Mehrjardi*

DOI: 10.2174/1570178619666220127123444

DownloadDownload PDF Flyer Cite As
Sulfonated Ethylenediamine Functionalized Magnetic Nanoparticles as a Highly Efficient Heterogeneous Nanocatalyst for the Green Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Page: [842 - 849] Pages: 8

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

In the present study, a new magnetically recyclable nanocatalyst, Fe3O4@SiO2@(CH2)3-en- SO3H/H2SO4, was prepared through the immobilization of sulfonated ethylenediamine on the silicacoated magnetite nanoparticles. The catalyst was fully characterized by several physicochemical techniques, including FT-IR, FESEM, TEM, EDS, VSM, XRD and TGA. The resultant nanocatalyst was then utilized in the green synthesis of 2,3-dihydroquinazolin-4(1H)-ones via the cyclocondensation reaction of various aldehydes and ketones with anthranilamide in refluxed EtOH. Short reaction times, high product yields, environmentally friendly reaction conditions, simple operation and reusability of the catalyst are important features of the present procedure. The catalyst can magnetically be recycled and reused several times without notable loss in the activity.

Keywords: Magnetic nanoparticles, heterogeneous catalyst, Fe3O4@SiO2@(CH2)3-en-SO3H/H2SO4, reusability, 2, 3- dihydroquinazolin-4(1H)-ones, nanocatalyst.

Graphical Abstract

[1]
Connolly, D.J.; Cusack, D.; O’Sullivan, T.P.; Guiry, P.J. Tetrahedron, 2005, 61, 10153.
[http://dx.doi.org/10.1016/j.tet.2005.07.010]
[2]
Marzaro, G.; Guiotto, A.; Pastorini, G.; Chilin, A. Tetrahedron, 2010, 66, 962.
[http://dx.doi.org/10.1016/j.tet.2009.11.091]
[3]
Shang, Y.H.; Fan, L.Y.; Li, X.X.; Liu, M.X. Chin. Chem. Lett., 2015, 26, 1355.
[http://dx.doi.org/10.1016/j.cclet.2015.07.026]
[4]
Horton, D.A.; Bourne, G.T.; Smythe, M.L. Chem. Rev., 2003, 103(3), 893-930.
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[5]
Li, S.W.; Nair, M.G.; Edwards, D.M.; Kisliuk, R.L.; Gaumont, Y.; Dev, I.K.; Duch, D.S.; Humphreys, J.; Smith, G.K.; Ferone, R. J. Med. Chem., 1991, 34(9), 2746-2754.
[http://dx.doi.org/10.1021/jm00113a011] [PMID: 1895294]
[6]
Su, W.; Yang, B. Aust. J. Chem., 2002, 55, 695.
[http://dx.doi.org/10.1071/CH02117]
[7]
Moore, J.A.; Sutherland, G.J.; Sowerby, R.; Kelly, E.G.; Palermo, S.; Webster, W. J. Org. Chem., 1969, 34, 887.
[http://dx.doi.org/10.1021/jo01256a024]
[8]
Khurana, J.M.; Kukreja, G. J. Heterocycl. Chem., 2003, 40, 677.
[http://dx.doi.org/10.1002/jhet.5570400419]
[9]
Rambabu, D.; Kumar, S.K.; Sreenivas, B.Y.; Sandra, S.; Kandale, A.; Misra, P.; Rao, M.V.B.; Pal, M. Tetrahedron Lett., 2013, 54, 495.
[http://dx.doi.org/10.1016/j.tetlet.2012.11.057]
[10]
Shaabani, A.; Maleki, A.; Mofakham, H. Synth. Commun., 2008, 38, 3751.
[http://dx.doi.org/10.1080/00397910802213802]
[11]
Shaterian, H.R.; Oveisi, A.R. Chin. J. Chem., 2009, 27, 2418.
[http://dx.doi.org/10.1002/cjoc.201090018]
[12]
Revathy, K.; Lalitha, A.J. Iran. Chem. Soc., 2015, 12, 2045.
[http://dx.doi.org/10.1007/s13738-015-0680-2]
[13]
Zong, Y.X.; Zhao, Y.; Luo, W.C.; Yu, X.H.; Wang, J.K.; Pan, Y. Chin. Chem. Lett., 2010, 21, 778.
[http://dx.doi.org/10.1016/j.cclet.2010.03.022]
[14]
Labade, V.B.; Shinde, P.V.; Shingare, M.S. Tetrahedron Lett., 2013, 54, 5778.
[http://dx.doi.org/10.1016/j.tetlet.2013.08.037]
[15]
Safaei, H.R.; Shekouhy, M.; Shafiee, V.; Davoodi, M. J. Mol. Liq., 2013, 180, 139.
[http://dx.doi.org/10.1016/j.molliq.2013.01.013]
[16]
Mirjalili, B.B.F.; Bamoniri, A.; Azad, S.J. Iran. Chem. Soc., 2017, 14, 47.
[http://dx.doi.org/10.1007/s13738-016-0956-1]
[17]
Chen, J.; Su, W.; Wu, H.; Liu, M.; Jin, C. Green Chem., 2007, 9, 972.
[http://dx.doi.org/10.1039/b700957g]
[18]
Davoodnia, A.; Allameh, S.; Fakhari, A.R.; Tavakoli-Hoseini, N. Chin. Chem. Lett., 2010, 21, 550.
[http://dx.doi.org/10.1016/j.cclet.2010.01.032]
[19]
Wang, J.; Zong, Y.; Fu, R.; Niu, Y.; Yue, G.; Quan, Z.; Wang, X.; Pan, Y. Ultrason. Sonochem., 2014, 21(1), 29-34.
[http://dx.doi.org/10.1016/j.ultsonch.2013.05.009] [PMID: 23751459]
[20]
Rostami, A.; Tahmasbi, B.; Gholami, H.; Taymorian, H. Chin. Chem. Lett., 2013, 24, 211.
[http://dx.doi.org/10.1016/j.cclet.2013.01.032]
[21]
Zhang, S.G.; Xie, Z.B.; Liu, L.S.; Liang, M.; Le, Z.G. Chin. Chem. Lett., 2017, 28, 101.
[http://dx.doi.org/10.1016/j.cclet.2016.06.001]
[22]
Beyki, M.; Fallah-Mehrjardi, M. Lett. Org. Chem., 2018, 15, 39.
[23]
Fallah-Mehrjardi, M.; Kalantari, S. Russ. J. Org. Chem., 2020, 56, 298.
[http://dx.doi.org/10.1134/S1070428020020207]
[24]
Fang, D.; Yang, J.; Zhang, H.; Jiao, C. J. Ind. Eng. Chem., 2011, 17, 386.
[http://dx.doi.org/10.1016/j.jiec.2010.09.028]
[25]
Goli-Jolodar, O.; Shirini, F.; Seddighi, M. Dyes Pigments, 2016, 133, 292.
[http://dx.doi.org/10.1016/j.dyepig.2016.06.001]
[26]
Kargar, H.; Fallah-Mehrjardi, M.; Behjatmanesh-Ardakani, R.; Munawar, K.S.; Ashfaq, M.; Tahir, M.N. Transition Met. Chem, 2021, 46, 437.
[27]
de Vos, D.E.; Sels, B.F.; Jacobs, P.A. Adv. Catal., 2001, 46, 1.
[http://dx.doi.org/10.1016/S0360-0564(02)46021-X]
[28]
Campisciano, V.; Giacalone, F.; Gruttadauria, M. Chem. Rec., 2017, 17(10), 918-938.
[http://dx.doi.org/10.1002/tcr.201700005] [PMID: 28444986]
[29]
Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J-M. Chem. Rev., 2011, 111(5), 3036-3075.
[http://dx.doi.org/10.1021/cr100230z] [PMID: 21401074]
[30]
Ma, W.; Ebadi, A.G.; Sabil, M.S.; Javahershenas, R.; Jimenez, G. RSC Advances, 2019, 9, 12801.
[http://dx.doi.org/10.1039/C9RA01679A]
[31]
Feng, G.; Hu, D.; Yang, L.; Cui, Y.; Cui, X.A.; Li, H. Separ. Purif. Tech., 2010, 74, 253.
[http://dx.doi.org/10.1016/j.seppur.2010.06.013]
[32]
Davarpanah, J.; Kiasat, A.R. Catal. Commun., 2013, 42, 98.
[http://dx.doi.org/10.1016/j.catcom.2013.07.040]
[33]
Najafi, F.; Fallah-Mehrjardi, M. Lett. Org. Chem., 2018, 15, 778.
[http://dx.doi.org/10.2174/1570178615666180126155640]
[34]
Talaei, H.; Fallah-Mehrjardi, M.; Hakimi, F. J. Chin. Chem. Soc. (Taipei), 2018, 65, 523.
[http://dx.doi.org/10.1002/jccs.201700401]
[35]
Fallah-Mehrjardi, M.; Kalantari, S. Org. Chem. Res., 2020, 6, 137.
[36]
Kiasat, A.R.; Davarpanah, J. J. Mol. Catal. Chem., 2013, 373, 46.
[http://dx.doi.org/10.1016/j.molcata.2013.03.003]
[37]
Kassaee, M.Z.; Masrouri, H.; Movahedi, F. Appl. Catal. A Gen., 2011, 395, 28.
[http://dx.doi.org/10.1016/j.apcata.2011.01.018]
[38]
Chen, J.X.; Wu, H.Y.; Su, W.K. Chin. Chem. Lett., 2007, 18, 536.
[http://dx.doi.org/10.1016/j.cclet.2007.03.037]
[39]
Abdollahi-Alibeik, M.; Shabani, E. Chin. Chem. Lett., 2011, 22, 1163.