Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives
Corresponding Author(s) : K. Kantharaju
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Traditionally, these reactions were performed in organic solvents and used expensive catalysts with elevated temperature. These catalytic media showed distinct properties during reaction course such as, in situ base, homogeneous catalysts and reducing agent. The present work reviewed green protocol synthesis of 2-amino-4H-chromene derivatives employing reaction of substituted benzaldehyde, malononitrile and α/β-naphthol or resorcinol; three component reaction catalyzed in the presence of water extract of banana peel ash (WEB) extraction under microwave and grindstone methods is described. The reaction found eco-friendly, simple reaction condition with easy separation of final product in pure form. The final product was characterized for its homogeneity using spectroscopic techniques. Some of the selected chromene derivatives (3b, 3d, 3g) prepared in this method is tested for its in vitro antimicrobial studies. The bioassay revealed that products 3b and 3d showed positive response and comparable antimicrobial activity with the reference compounds.
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- M. Sarmah, A. Dewan, M. Mondal, A.J. Thakur and U. Bora, RSC Adv., 6, 28981 (2016); https://doi.org/10.1039/C6RA00454G.
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- H.D. Isenberg, Clinical Microbiology Procedures Handbook, American Society For Microbiology: Washington, D.C, vol. 1 (1992)
References
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M. Sarmah, A. Dewan, M. Mondal, A.J. Thakur and U. Bora, RSC Adv., 6, 28981 (2016); https://doi.org/10.1039/C6RA00454G.
M. Konwar, A.A. Ali and D. Sarma, Tetrahedron Lett., 57, 2283 (2016); https://doi.org/10.1016/j.tetlet.2016.04.041.
W. Rattanavichai and W. Cheng, Fish Shellfish Immunol., 39, 326 (2014); https://doi.org/10.1016/j.fsi.2014.05.031.
P.R. Boruah, A.A. Ali, B. Saikia and D. Sarma, Green Chem., 17, 1442 (2015); https://doi.org/10.1039/C4GC02522A.
I.O. Olabanji, E.A. Oluyemi and O.S. Ajayi, Afr. J. Biotechnol., 11, 16512 (2012).
S. Laskar, G. Brahmachari, J. Org. Biomol. Chem., 2, 1 (2014).
K. Görlitzer, A. Dehne and E. Engler, Arch. Pharm., 316, 264 (1983); https://doi.org/10.1002/ardp.19833160315.
M. Brunavs, C. P. Dell, P. T. Gallagher, W. M. Owton and C. W. Smith, Eur. Pat. Appl. EP, 557075 A1 19930825 (1993).
M. Kidwai, S. Saxena, M.K. Rahman Khan and S.S. Thukral, Bioorg. Med. Chem. Lett., 15, 4295 (2005); https://doi.org/10.1016/j.bmcl.2005.06.041.
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R.E. Dolle, J. Comb. Chem., 5, 693 (2003); https://doi.org/10.1021/cc0340224.
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S.V. Goswami, S.S. Pendalwar and S.R. Bhusare, Chem. Biol. Interact., 6, 171 (2016).
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M. Costa, F. Areias, L. Abrunhosa, A. Venâncio and F. Proença, J. Org. Chem., 73, 1954 (2008); https://doi.org/10.1021/jo702552f.
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V.P. Pagore, S.U. Tekale and B.D. Rupnar, J. Chem. Pharm. Res., 7, 1057 (2015).
N.K. Shah, N.M. Shah, M.P. Patel and R.G. Patel, J. Chem. Sci., 125, 525 (2013); https://doi.org/10.1007/s12039-013-0421-y.
R.S. Varma, Pure Appl. Chem., 73, 193 (2001); https://doi.org/10.1351/pac200173010193.
T.X.T. Luu, P. Christensen, F. Duus and T.N. Le, Synth. Commun., 38, 2011 (2008); https://doi.org/10.1080/00397910801997819.
R.S. Varma, K.P. Naicker and P.J. Liesen, Tetrahedron Lett., 39, 8437 (1998); https://doi.org/10.1016/S0040-4039(98)01922-4.
M.K. Mohammadi, Open J. Synth. Theory Appl., 2, 87 (2013); https://doi.org/10.4236/ojsta.2013.23011.
E. Parquet and Q. Lin, J. Chem. Educ., 74, 1225 (1997); https://doi.org/10.1021/ed074p1225.
A. Walia, S. Kang and R.B. Silverman, J. Org. Chem., 78, 10931 (2013); https://doi.org/10.1021/jo401778e.
V.H. Jadhav, H.B. Borate and R.D. Wakharkar, Indian J. Chem., 45B, 322 (2006).
I. Saxena, N. Deka, J.C. Sarma and S. Tsuboi, Synth. Commun., 33, 4185 (2003); https://doi.org/10.1081/SCC-120026335.
M. Bessieres, V. Roy and L.A. Agrofoglio, RSC Adv., 4, 59747 (2014); https://doi.org/10.1039/C4RA13033B.
K. Selvakumar, K.A. Prasath Lingam and R.V. Luxmi Varma, RSC Adv., 4, 36538 (2014); https://doi.org/10.1039/C4RA06841F.
M.B. Gawande, S.N. Shelke, R. Zboril and R.S. Varma, Acc. Chem. Res., 47, 1338 (2014); https://doi.org/10.1021/ar400309b.
G. Brahmachari, K. Nurjamal, I. Karmakar, S. Begam, N. Nayek and B. Mandal, ACS Sustain. Chem. Eng., 5, 9494 (2017); https://doi.org/10.1021/acssuschemeng.7b02696.
H.D. Isenberg, Clinical Microbiology Procedures Handbook, American Society For Microbiology: Washington, D.C, vol. 1 (1992)