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A Facile Solvent-Free Route for One-Pot Multicomponent Synthesis of Benzylpyrazolyl Coumarins Derivatives in Presence of Effective Synergetic Catalytic System
Corresponding Author(s) : Narendra R. Kamble
Asian Journal of Chemistry,
Vol. 31 No. 6 (2019): Vol 31 Issue 6
Abstract
A combinatorial library of benzylpyrazolyl coumarin derivatives have been synthesized by a green one-pot four-component reaction between aryl hydrazine/hydrazine hydrate (1), ethyl acetoacetate (2), aromatic aldehydes (3) and 4-hydroxycoumarin (4) catalyzed by niobium pentachloride with silver salt under solvent-free conditions has been developed. Experimental simplicity, simple work-up procedure and solvent-free reaction condition at room temperature are important features of the present protocol.
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References
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J. Zhu and H. Bienayme, Multicomponent Reaction, Wiley-VCH: Weinheim (2005).
D.J. Ramón and M. Yus, Angew. Chem. Int. Ed., 44, 1602 (2005); https://doi.org/10.1002/anie.200460548.
A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009); https://doi.org/10.1021/cr800448q.
M.C. Pirrung and K.D. Sarma, J. Am. Chem. Soc., 126, 444 (2004); https://doi.org/10.1021/ja038583a.
C.-J. Li, Chem. Rev., 93, 2023 (1993); https://doi.org/10.1021/cr00022a004.
C.-J. Li, Chem. Rev., 105, 3095 (2005); https://doi.org/10.1021/cr030009u.
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); https://doi.org/10.1021/cr940089p.
S. Hesse and G. Kirsch, Tetrahedron Lett., 43, 1213 (2002); https://doi.org/10.1016/S0040-4039(01)02373-5.
B.H. Lee, M.F. Clothier, F.E. Dutton, G.A. Conder and S.S. Johnson, Bioorg. Med. Chem. Lett., 8, 3317 (1998); https://doi.org/10.1016/S0960-894X(98)00588-5.
J.-C. Jung, Y.-J. Jung and O.-S. Park, Synth. Commun., 31, 1195 (2001); https://doi.org/10.1081/SCC-100104003.
G. Melagraki, A. Afantitis, O. Igglessi-Markopoulou, A. Detsi, M. Koufaki, C. Kontogiorgis and D.J. Hadjipavlou-Litina, Eur. J. Med. Chem., 44, 3020 (2009); https://doi.org/10.1016/j.ejmech.2008.12.027.
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M. Himly, B. Jahn-Schmid, K. Pittertschatscher, B. Bohle, K. Grubmayr, F. Ferreira, H. Ebner and C.J. Ebner, Allergy Clin. Immunol., 111, 882 (2003); https://doi.org/10.1067/mai.2003.163.
T. Watanabe, S. Yuki, M. Egawa and H. Nishi, J. Pharmacol. Exp. Ther., 268, 1597 (1994).
H. Kawai, H. Nakai, M. Suga, S. Yuki, T. Watanabe and K.I. Saito, J. Pharmacol. Exp. Ther., 281, 921 (1997).
T.W. Wu, L.H. Zeng, J. Wu and K.P. Fung, Life Sci., 71, 2249 (2002); https://doi.org/10.1016/S0024-3205(02)01965-3.
M.A. Al-Haiza, S.A. El-Assiery and G.H. Sayed, Acta Pharm., 51, 251 (2001).
D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi and M. Botta, Bioorg. Med. Chem., 17, 5716 (2009); https://doi.org/10.1016/j.bmc.2009.05.058.
M. Radi, V. Bernardo, B. Bechi, D. Castagnolo, M. Pagano and M. Botta, Tetrahedron Lett., 50, 6572 (2009); https://doi.org/10.1016/j.tetlet.2009.09.047.
F. Moreau, N. Desroy, J.M. Genevard, V. Vongsouthi, V. Gerusz, G. Le Fralliec, C. Oliveira, S. Floquet, A. Denis, S. Escaich, M. Busemann, K. Wolf and A. Aschenbrenner, Bioorg. Med. Chem. Lett., 18, 4022 (2008); https://doi.org/10.1016/j.bmcl.2008.05.117.
F.A. Pasha, M. Muddassar, M.M. Neaz and S.J. Cho, J. Mol. Graph. Model., 28, 54 (2009); https://doi.org/10.1016/j.jmgm.2009.04.006.
C.E. Rosiere and M.I. Grossman, Science, 113, 651 (1951); https://doi.org/10.1126/science.113.2945.651.
D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice and M.E. Feigenson, J. Med. Chem., 28, 256 (1985); https://doi.org/10.1021/jm00380a020.
P.M.S. Chauhan, S. Singh and R.K. Chatterjee, Indian J. Chem., 32B, 858 (1993).
P. Gunasekaran, S. Perumal, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4530 (2011); https://doi.org/10.1016/j.ejmech.2011.07.029.
P.P. Ghosh, G. Pal, S. Paul and A.R. Das, Green Chem., 14, 2691 (2012); https://doi.org/10.1039/c2gc36021g.
S. Yaragorla, A. Pareek and R. Dada, Tetrahedron Lett., 56, 4770 (2015); https://doi.org/10.1016/j.tetlet.2015.06.049.
R.K. Pardeshi, S.A. Jadhav, M.G. Shioorkar, A.P. Sarkate and D.B. Shinde, Chem. Mater. Res., 7, 105 (2015).