New Crown Ether-Based Ionic Liquids as a Green and Versatile Organocatalyst for Three-Component Synthesis of 1,5-Dihydropyrano[2,3- c]chromene Derivatives

Author(s): Iman Mohammadzadeh, Ali Asadipour, Abbas Pardakhty, Mehdi Abaszadeh*.

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 3 , 2020

DOI : 10.2174/1570178616666190620124947

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Abstract:

A simple and green method for the synthesis of 1,5-dihydropyrano[2,3-c]chromene derivatives has been reported by three-component reaction of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin in the presence of a series of novel crown ether-based ionic liquids (CE-based ILs) in H2O/EtOH (1:1), under the reflux conditions. The novel CE-based ILs have been synthesized by 18-crown-6 or dibenzo 18-crown-6 chelated with sodium benzenesulfinate derivatives and used as a green and environmental organocatalyst. This method has some advantages such as the aqueous reaction medium, stable catalysts, cleaner reaction profiles and high yield of products in short reaction time.

Keywords: Dihydropyrano[2, 3-c]chromene, ionic liquids, sodium benzenesulfinates, crown ethers, three component reactions, aromatic aldehydes.

[1]
Hardacre, C.; Parvulescu, V. Catalysis in Ionic Liquids From Catalyst Synthesis to Application. ; In: ; Royal Society of Chemistry,; 1st ed; Cambridge,. , 2014.
[http://dx.doi.org/10.1039/9781849737210]
[2]
Keskin, S.; Kayrak-Talay, D.; Akman, U.; Hortaçsu, Ö. J. Supercrit. Fluids, 2007, 43, 150-180.
[http://dx.doi.org/10.1016/j.supflu.2007.05.013]
[3]
Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S.M.S. Tetrahedron, 2005, 61, 1015-1060.
[http://dx.doi.org/10.1016/j.tet.2004.10.070]
[4]
Andrade-Neto, V.F.; Goulart, M.O.F.; Silva Filho, J.F.; Silva, M.J.; Pinto, M.C.F.R.; Pinto, A.V.; Zalis, M.G.; Carvalho, L.H.; Krettli, A.U. Bioorg. Med. Chem. Lett., 2004, 14, 1145-1149.
[http://dx.doi.org/10.1016/j.bmcl.2003.12.069] [PMID: 14980653]
[5]
Ellis, G.P. In The Chemistry of Heterocyclic of Compounds. Chromenes, Chromanes and Chromones; In:. John Wiley,; 1st ed; New York,, 1977.
[http://dx.doi.org/10.1002/9780470187012]
[6]
Xiao, Y.; Malhotra, S. Tetrahedron Lett., 2004, 45, 8339-8342.
[http://dx.doi.org/10.1016/j.tetlet.2004.09.070]
[7]
Hafez, E.A.A.; Elnagdi, M.H.; Elagemey, A.G.A.; El-Taweel, F.M.A.A. Heterocycles, 1987, 26, 903-907.
[http://dx.doi.org/10.3987/R-1987-04-0903]
[8]
DeCastro, C.; Sauvage, E.; Valkenberg, M.H.; Hölderich, W.F. J. Catal., 2000, 196, 86-94.
[http://dx.doi.org/10.1006/jcat.2000.3004]
[9]
Sarca, V.D.; Laali, K.K. Green Chem., 2004, 6, 245-248.
[http://dx.doi.org/10.1039/b400113c]
[10]
Song, Y.; Jing, H.; Li, B.; Bai, D. Chemistry, 2011, 17(31), 8731-8738.
[http://dx.doi.org/10.1002/chem.201100112] [PMID: 21678504]
[11]
Zhu, J.; Bienayme´, H. Multicomponent Reactions. In: Wiley-VCH,; 1st ed; Weinheim, , 2005.
[http://dx.doi.org/10.1002/3527605118]
[12]
Kazemizadeh, A.R.; Ramazani, A. J. Braz. Chem. Soc., 2009, 20, 309-312.
[http://dx.doi.org/10.1590/S0103-50532009000200016]
[13]
Tietze, L.F. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
[14]
Alizadeh, A.; Roosta, A. Chem. Pap., 2018, 72, 2467-2478.
[http://dx.doi.org/10.1007/s11696-018-0497-4]
[15]
Stalling, T.; Pauly, J.; Kröger, D.; Martens, J. Tetrahedron, 2015, 71, 8290-8301.
[http://dx.doi.org/10.1016/j.tet.2015.08.073]
[16]
Kidwai, M.; Saxena, S.; Khan, M.K.; Thukral, S.S. Bioorg. Med. Chem. Lett., 2005, 15(19), 4295-4298.
[http://dx.doi.org/10.1016/j.bmcl.2005.06.041] [PMID: 16040241]
[17]
Kumar, A.; Maurya, R.A.; Sharma, S.; Ahmad, P.; Singh, A.B.; Bhatia, G.; Srivastava, A.K. Bioorg. Med. Chem. Lett., 2009, 19(22), 6447-6451.
[http://dx.doi.org/10.1016/j.bmcl.2009.09.031] [PMID: 19811915]
[18]
Raj, T.; Bhatia, R.K.; Kapur, A.; Sharma, M.; Saxena, A.K.; Ishar, M.P.S. Eur. J. Med. Chem., 2010, 45(2), 790-794.
[http://dx.doi.org/10.1016/j.ejmech.2009.11.001] [PMID: 19939522]
[19]
Symeonidis, T.; Fylaktakidou, K.C.; Hadjipavlou-Litina, D.J.; Litinas, K.E. Eur. J. Med. Chem., 2009, 44(12), 5012-5017.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.004] [PMID: 19781823]
[20]
Raj, T.; Bhatia, R.K.; Sharma, R.K.; Gupta, V.; Sharma, D.; Ishar, M.P.S. Eur. J. Med. Chem., 2009, 44(8), 3209-3216.
[http://dx.doi.org/10.1016/j.ejmech.2009.03.030] [PMID: 19375826]
[21]
Ough, M.; Lewis, A.; Bey, E.A.; Gao, J.; Ritchie, J.M.; Bornmann, W.; Boothman, D.A.; Oberley, L.W.; Cullen, J.J.J. Cancer Biol. Ther., 2005, 4(1), 95-102.
[http://dx.doi.org/10.4161/cbt.4.1.1382] [PMID: 15662131]
[22]
Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Curr. Med. Chem., 2006, 13(2), 199-222.
[http://dx.doi.org/10.2174/092986706775197890] [PMID: 16472213]
[23]
Abaszadeh, M.; Seifi, M. J. Sulfur Chem., 2017, 38, 440-449.
[http://dx.doi.org/10.1080/17415993.2017.1293058]
[24]
Abaszadeh, M.; Seifi, M.; Asadipour, A. Res. Chem. Intermed., 2015, 41, 5229-5238.
[http://dx.doi.org/10.1007/s11164-014-1624-7]
[25]
Abaszadeh, M.; Seifi, M. Lett. Org. Chem., 2015, 12, 271-276.
[http://dx.doi.org/10.2174/1570178612666150203004727]
[26]
Amirheidari, B.; Seifi, M.; Abaszadeh, M. Res. Chem. Intermed., 2016, 42, 3413-3423.
[http://dx.doi.org/10.1007/s11164-015-2220-1]
[27]
Abaszadeh, M.; Seifi, M.; Asadipour, A. Synth. React. Inorg. Met.-Org. Chem., 2016, 46, 512-517.
[http://dx.doi.org/10.1080/15533174.2014.988812]
[28]
Abaszadeh, M.; Seifi, M.; Ebrahimipour, S.Y. Bull. Chem. Soc. Ethiop., 2016, 30, 253-262.
[http://dx.doi.org/10.4314/bcse.v30i2.9]
[29]
Pourshojaei, Y.; Jadidi, M.H. Eskandari. K.; Foroumadi, A.R.; Asadipour, A. Res. Chem. Intermed., 2018, 44, 4195-4212.
[http://dx.doi.org/10.1007/s11164-018-3363-7]
[30]
Paul, S.; Bhattacharyya, P.; Das, A.R. Tetrahedron Lett., 2011, 52, 4636-4641.
[http://dx.doi.org/10.1016/j.tetlet.2011.06.101]
[31]
Paul, S.; Ghosh, S.; Bhattacharyya, P.; Das, A.R. RSC Advances, 2013, 3, 14254-14262.
[http://dx.doi.org/10.1039/c3ra42352b]


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Article Details

VOLUME: 17
ISSUE: 3
Year: 2020
Page: [240 - 245]
Pages: 6
DOI: 10.2174/1570178616666190620124947
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