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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

[Bmim]HSO4 loaded on Graphene Oxide: A Green and Retrievable Nanocatalyst for the Synthesis of Polysubstituted Pyrroles; Some of Which are Fluorinated

Author(s): Maral Shekarchi and Farahnaz K. Behbahani*

Volume 18, Issue 4, 2021

Published on: 01 June, 2020

Page: [294 - 302] Pages: 9

DOI: 10.2174/1570178617999200601170128

Price: $65

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Abstract

1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4 as a non-halogenated ionic liquid was loaded on graphene oxide ([bmim]HSO4/GO) and employed as a green, reusable, solid nanocatalyst for the preparation of polysubstituted pyrroles in the presence of amines (such as benzeneamine, 2-amino-4-methylthiazole, adenine (9H-purin-6-amine)), benzaldehydes or cinnamaldehyde or furfural, 1,3-dicarbonyl compounds, and nitromethane at 90-95°C. The advantages of this protocol are the synthesis of some novel polysubstituted pyrroles containing fluorine atoms, thiazole and adenine nuclei that are very important in pharmaceutical and drug discovery research in comparison to previously reported results.

Keywords: [bmim] HSO4/GO, graphene oxide (GO), multicomponent reactions, pyrroles.

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[1]
Das, D.; Sikdar, P.; Bairagi, M. Eur. J. Med. Chem., 2016, 109, 89-98.
[http://dx.doi.org/10.1016/j.ejmech.2015.12.022] [PMID: 26771245]
[2]
Idhayadhulla, A.; Kumar, R.S.; Nasser, A.J.A.; Manilal, A. Bull. Chem. Soc. Ethiop., 2012, 26, 429-435.
[http://dx.doi.org/10.4314/bcse.v26i3.12]
[3]
Padron, J.M.; Tejedor, D.; Santos-Exposito, A.; Garcia-Tellado, F.; Martin, V.S.J. Bioorg. Med. Chem. Lett., 2005.1524872490
[http://dx.doi.org/10.1016/j.bmcl.2005.03.069]
[4]
Lehuédé, J.; Fauconneau, B.; Barrier, L.; Ourakow, M.; Piriou, A.; Vierfond, J. Eur. J. Med. Chem., 1999, 34(11), 991-996.
[http://dx.doi.org/10.1016/S0223-5234(99)00111-7] [PMID: 10889322]
[5]
Khan, A.T.; Lal, M.; Bagdi, P.R.; Basha, R.S.; Saravanan, P.; Patra, S. Tetrahedron Lett., 2012, 53, 4145-4150.
[http://dx.doi.org/10.1016/j.tetlet.2012.05.133]
[6]
Hua, H-C.; Liub, Y-H.; Lia, B-L.; Cuia, Z-S.; Zhang, Z-H. RSC Advances, 2015, 5, 7720-7728.
[http://dx.doi.org/10.1039/C4RA13577F]
[7]
Gajengi, A.L.; Bhanage, B.M. Catal. Lett., 2016, 146, 1341-1347.
[http://dx.doi.org/10.1007/s10562-016-1762-1]
[8]
Kumar, S.; Verma, N.; Ahmed, N. J. Saudi Chem. Soc., 2018, 22, 136-145.
[http://dx.doi.org/10.1016/j.jscs.2016.01.005]
[9]
Gupta, N.; Singh, K.N.; Singh, J. J. Mol. Liq., 2014, 199, 470-473.
[http://dx.doi.org/10.1016/j.molliq.2014.07.038]
[10]
Reddy, G.R.; Reddy, T.R.; Joseph, S.C.; Reddy, K.S.; Reddy, L.S.; Kumar, P.M.; Krishna, G.R.; Reddy, C.M.; Rambabu, D.; Kapavarapu, R.; Lakshmi, C.; Meda, T.; Priya, K.K.; Parsa, K.V.; Pal, M. Chem. Commun. (Camb.), 2011, 47(27), 7779-7781.
[http://dx.doi.org/10.1039/c1cc12321a] [PMID: 21643571]
[11]
Reddy, G.R.; Reddy, T.R.; Joseph, S.C.; Reddy, K.S.; Pal, M. RSC Advances, 2012, 2, 3387-3395.
[http://dx.doi.org/10.1039/c2ra00982j]
[12]
Atar, A.B.; Tae Jeong, Y. Tetrahedron Lett., 2013, 54, 5624-5628.
[http://dx.doi.org/10.1016/j.tetlet.2013.08.016]
[13]
Silveira, C.C.; Mendes, S.R.; Martins, G.M.; Schlosser, S.C.; Kaufman, T.S. Tetrahedron, 2013, 69, 9076-9085.
[http://dx.doi.org/10.1016/j.tet.2013.08.035]
[14]
Li, B-L.; Li, P-H.; Fang, X-N.; Li, C-X.; Sun, J-L.; Mo, L-P.; Zhang, Z-H. Tetrahedron, 2013, 69, 7011-7018.
[http://dx.doi.org/10.1016/j.tet.2013.06.049]
[15]
Murthi, P.R.K.; Rambabu, D.; Rao, M.V.B.; Pal, M. Tetrahedron Lett., 2014, 55, 507-509.
[http://dx.doi.org/10.1016/j.tetlet.2013.11.073]
[16]
Li, B-L.; Zhang, M.; Hu, H-C.; Dub, X.; Zhang, Z-H. New J. Chem., 2014, 38, 2435-2442.
[http://dx.doi.org/10.1039/c3nj01368e]
[17]
Meshram, H.M.; Babu, B.M.; Kumar, G.S.; Thakur, P.B.; Bangade, V.M. Tetrahedron Lett., 2013, 54, 2296-2302.
[http://dx.doi.org/10.1016/j.tetlet.2013.01.098]
[18]
Moghaddam, F.M.; Foroushani, B.K.; Rezvani, H.R. RSC Advances, 2015, 5, 18092-18096.
[http://dx.doi.org/10.1039/C4RA09348H]
[19]
Hamrahian, S.A.; Rakhtshah, J.; Davijani, S.M.M.; Salehzadeh, S. Appl. Organomet. Chem., 2018, 32e4501,
[http://dx.doi.org/10.1002/aoc.4501]
[20]
Saeidian, H.; Abdoli, M.; Salimi, R. C. R. Chim., 2013, 16, 1063-1070.
[http://dx.doi.org/10.1016/j.crci.2013.02.008]
[21]
Gajengi, A.L.; Fernandes, C.S.; Bhanage, B.M. Mol. Catal, 2018, 451, 13-19.
[http://dx.doi.org/10.1016/j.mcat.2017.10.010]
[22]
Bagdi, P.R.; Basha, R.S.; Lal, M.; Khan, A.T. Chem. Lett., 2013, 42, 939-941.
[http://dx.doi.org/10.1246/cl.130317]
[23]
Maiti, S.; Biswas, S.; Jana, U. J. Org. Chem., 2010, 75(5), 1674-1683.
[http://dx.doi.org/10.1021/jo902661y] [PMID: 20131775]
[24]
Konkala, K.; Chowrasia, R.; Manjari, P.S.; Domingues, N.L.C.; Katla, R. RSC Advances, 2016, 6, 43339-43344.
[http://dx.doi.org/10.1039/C6RA08335H]
[25]
Bharate, J.B.; Sharma, R.; Aravinda, S.; Gupta, V.K.; Singh, B.; Bharatea, S.B.; Vishwakarma, R.A. RSC Advances, 2013, 3, 21736-21742.
[http://dx.doi.org/10.1039/c3ra43324b]
[26]
Shinde, V.V.; Lee, S.D.; Jeong, Y.S.; Jeong, Y.T. Tetrahedron Lett., 2015, 56, 859-865.
[http://dx.doi.org/10.1016/j.tetlet.2014.12.126]
[27]
Anari, M.S.; Behbahani, F.K. Leban. Sci. J., 2017, 18, 219-225.
[28]
Mohammadi, B.; Behbahani, F.K. Mol. Divers., 2018, 22(2), 405-446.
[http://dx.doi.org/10.1007/s11030-017-9806-z] [PMID: 29349521]
[29]
Behbahani, F.K.; Ziaei, P.; Fakhroueian, Z.; Doragi, N. Monatsh. Chem., 2011, 142, 901-906.
[http://dx.doi.org/10.1007/s00706-011-0523-5]
[30]
Behbahani, F.K.; Alaei, H.S. J. Chem. Sci., 2013, 125, 623-626.
[http://dx.doi.org/10.1007/s12039-013-0419-5]
[31]
Wang, Y.; Sang, R.; Zheng, Y.; Guo, L.; Guan, M.; Wu, Y. Catal. Commun., 2017, 89, 138-142.
[http://dx.doi.org/10.1016/j.catcom.2016.09.027]
[32]
Jagadhane, P.B.; Jadhav, N.C.; Herlekar, O.P.; Telvekar, V.N. Synth. Commun., 2015, 45, 2130-2134.
[http://dx.doi.org/10.1080/00397911.2015.1066392]
[33]
Goyal, S.; Patel, J.K.; Gangar, M.; Kumar, K.; Nair, V.A. RSC Advances, 2015, 5, 3187-3195.
[http://dx.doi.org/10.1039/C4RA09873K]

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