Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Hyperactive Magnetically Separable Nano-sized MgFe2O4 Catalyst for the Synthesis of Several Five- and Six-Membered Heterocycles

Shobha Bansal, Yogendra Kumar, Dipak Kumar Das, Prabal Pratap Singh
Affiliation: 
Department of Chemistry, GLA University, 17km stone, NH-2 Delhi-Mathura Highway, Chaumuhan, Mathura UP 281406, India prabal.singh@gla.ac.in
DOI: 
https://doi.org/10.23939/chcht13.02.163
AttachmentSize
PDF icon full_text.pdf451.19 KB

Keywords:

Abstract: 
MgFe2O4 nanoparticle ferrites were synthesized by combustion technique using pure ferric nitrate and magnesium nitratecarbonate. The magnetically separable MgFe2O4 MNP’s were found to be hyper active catalyst for the synthesis of a wide range of biologically active five and six-membered heterocyclic moieties at refluxing conditions. Reaction times are lowest in comparison to all reported in literature with excellent yields. Strong electron pull of Fe3+ is responsible for its hyper activity, which has been substantiated by substitution of Fe3+ by other trivalent metal ions. Mg2+ has a unique role because replacement of Mg2+ has poor catalytic activity. The developed protocol has been efficiently utilized for the synthesis of a series of substituted mono/bis pyrimidines, pyrimidin-2-ol, pyrimidin-2-thiol, pyrazoles and isoxazoles by condensing monochalcones/1,4-bischalcones with various bis-nucleophiles in the presence of catalytic amount of heterogenous magnetic MgFe2O4 nanoparticles. The structure of these synthesized compounds was determined by FTIR, 1H, 13C and mass spectra. The catalyst can be removed easily from reaction mixture by using a simple external magnet. Nanoparticles of ferrite were recovered and reused with no appreciable change in the activity even after the five runs. Nanoparticles are characterized by XRD, TEM and IR spectroscopy.
References: 

[1] Gardimalla H., Mandal D., Stevens P. et al.: Chem. Commun., 2005, 4432. https://doi.org/10.1039/b504128g
[2] Abu-Rezig R., Alper H., Wang D., Post M.: J. Am. Chem. Soc., 2006, 128, 5279. https://doi.org/10.1021/ja060140u
[3] Phan N., Gill C., Nguyen J. et al.: Angew. Chem. Int. Ed., 2006, 45, 2209. https://doi.org/10.1002/anie.200503445
[4] Baruwati B., Guin S.: Org. Lett., 2007, 9, 5377. https://doi.org/10.1021/ol702064x
[5] Shokouhimehr M., Piao Y., Kim J. et al.: Angew. Chem. Int. Ed., 2007, 46, 7039. https://doi.org/10.1002/anie.200702386
[6] Chouhan G., Wang D., Alper H.: Chem. Commun., 2007, 4809. https://doi.org/10.1039/b711298j
[7] Liu J., Peng X., Sun W. et al.: Org. Lett., 2008, 10, 3933. https://doi.org/10.1021/ol801478y
[8] Zheng X.,. Luo S., Zhang L., Cheng J.: Green Chem., 2009, 11, 455. https://doi.org/10.1039/b823123k
[9] Lu A-H., Salabas E., Schuth F.: Angew. Chem. Int. Ed., 2007, 46, 1222. https://doi.org/10.1002/anie.200602866
[10] Kassaee M., Masrouri H., Movahedi F.: Appl. Catal. A, 2011, 395, 28. https://doi.org/10.1016/j.apcata.2011.01.018
[11] Esmaeilpour M., Sardarian A., Javidi J.: Appl. Catal. A, 2012, 445-446, 359. https://doi.org/10.1016/j.apcata.2012.09.010
[12] Maleki A.: Tetrahedron Lett., 2013, 54, 2055. https://doi.org/10.1016/j.tetlet.2013.01.123
[13] Kiasat A., Davarpanah J.: J. Mol. Catal. A, 2013, 373, 46. https://doi.org/10.1016/j.molcata.2013.03.003
[14] Zamani F., Izadi E.: Catal. Commun., 2013, 42, 104. https://doi.org/10.1016/j.catcom.2013.08.006
[15] Gawande M., Bonifácio V., Varma R. et al.: Green Chem., 2013, 15, 1226. https://doi.org/10.1039/c3gc40375k
[16] Mahmoudi H., Jafari A.: Chem. Cat. Chem., 2013, 5, 3743. https://doi.org/10.1002/cctc.201300623
[17] Nemati F., Heravi M., Rad R.: Chin. J. Catal., 2012, 33, 1825. https://doi.org/10.1016/S1872-2067(11)60455-5
[18] Du Q., Zhang W., Ma H. et al.: Tetrahedron, 2012, 68, 3577. https://doi.org/10.1016/j.tet.2012.03.008
[19] Yang H., Li S., Wang X. et al.: J. Mol. Catal. A, 2012, 363–364, 404. https://doi.org/10.1016/j.molcata.2012.07.017
[20] Li W., Zhang B., Li X. et al.: Appl. Catal. A, 2013, 459, 65. https://doi.org/10.1016/j.apcata.2013.04.010
[21] Hu A., Yee G., Lin W.: J. Am. Chem. Soc., 2005,127, 12486. https://doi.org/10.1021/ja053881o
[22] Wang P., Kong A., Wang W. et al.: Catal. Lett., 2010, 135, 159. https://doi.org/10.1007/s10562-010-0271-x
[23] Gawande M., Rathi A., Nogueira I. et al.: Green Chem., 2013, 15, 1226. https://doi.org/10.1039/c3gc40375k
[24] Atashkar B., Rostami A., Tahmasbi B.: Catal. Sci. Tech., 2013, 3, 2140. https://doi.org/10.1039/c3cy00190c
[25] Alizadeh A., Khodaei M., Beygzadeh M. et al.: Bull. Korean Chem. Soc., 2012, 33, 2546. https://doi.org/10.5012/bkcs.2012.33.8.2546
[26] Cheng L., Li H., Sun J. et al.: Bioorg. Med. Chem., 2010, 18, 4606. https://doi.org/10.1016/j.bmc.2010.05.034
[27] Bhatt R.: J. Global Pharma. Tech., 2010, 2, 110.
[28] Kappe C., Shishkin O., Uraya G., Verdinoa P.: Tetrahedron, 2000, 56, 1859. https://doi.org/10.1016/S0040-4020(00)00116-2
[29] Amrutkar S., Bhagat U., Pargharmol P. et al.: Int. Pharm. Pharm. Sci.ence 2010, 2, 84.
[30] Atwal K., Swanson B., Unger S. et al.: J. Med. Chem. 1991, 34, 2248. https://doi.org/10.1021/jm00106a048
[31] Kudo N., Futura S.: Chem. Pharma. Bull., 1999, 47, 857. https://doi.org/10.1248/cpb.47.857
[32] Bonsei M., Loizzo M., Statti G. et al.: Bioorg. Med. Chem. Lett., 2010, 20, 1990. https://doi.org/10.1016/j.bmcl.2010.01.113
[33] Yar M., Abdullah M., Majeed J.: World Acad. Sci. Eng. Tech., 2006, 55, 593.
[34] Siddiqui S., Azam A.: Med. Chem. Res., 2014, 23, 2976. https://doi.org/10.1007/s00044-013-0877-9
[35] Kanagarajan V., Thanusu J., Gopalakrishna M.: Eur. J. Med. Chem., 2010, 45, 1583. https://doi.org/10.1016/j.ejmech.2009.12.068
[36] Thanh N., Mai N.: Carbohyd. Res., 2009, 344, 2399. https://doi.org/10.1016/j.carres.2009.09.002
[37] Bhat A., Arshad M., Lee E. et al.: Chem. Biodiver., 2013, 10, 2267. https://doi.org/10.1002/cbdv.201300009
[38] Hasan A., Khaleeq M., Raizi U.: J. Org. Chem., 2010, 22, 5581.
[39] Butta R., Donthamsetty S., Adivireddy P., Venkatapuram P.: J. Heterocycl. Chem., 2017, 54, 524. https://doi.org/10.1002/jhet.2615
[40] Kanagarajan V., How G. A., Siu C. N., Gopalkrishnan M.: J. Heterocycl. Chem., 2013, 50, 396. https://doi.org/10.1002/jhet.1046.
[41] Singh J., Dulawat M., Jaitawat N. et al.: Ind. J. Chem., 2012, 51B, 1623.
[42] Varga L., Nagy T., Kovesdi I. et al.: Tetrahedron, 2003, 59, 655. https://doi.org/10.1016/S0040-4020(02)01560-0
[43] Ghoneim A., El-Farargy A.: Org. Chem Curr. Res., 2016, 5, 1. https://doi.org/10.4172/2161-0401.1000159
[44] Jetti S., Verma D., Jain S.: ISRN Org. Chem., 2012. https://doi.org/10.5402/2012/480989
[45] Fazaeli R., Aliyan H., Mallakpour S. et al.: Chin. J. Catal., 2011, 32, 582. https://doi.org/10.1016/S1872-2067(10)60203-3
[46] Fazaeli R., Aliyan H., Bordbar M., Mohammadi E.: The Open Catal. J., 2010, 3, 79. https://doi.org/10.2174/1876214X01003010079
[47] Aliyan H., Fazaeli R., Tajsaeed N.: Iranian J. Catal. 2013, 3, 99.
[48] Maleki B., Azarifar D., Moghaddam A. et al.: J. Serb. Chem. Soc., 2009, 74, 1371. https://doi.org/10.2298/JSC0912371M
[49] Pinto D., Silva A., Cavaleiro J., Elguero J.: Eur. J. Org. Chem., 2003, 4, 747. https://doi.org/10.1002/ejoc.200390117
[50] Kavitha N., Divekar K., Priyadarshani B., Gajanan S., Manjunath M.: Der Pharma Chemica, 2011, 3, 55.