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An Efficient and Facile Synthesis of Novel Triazole C-N Linked Chromone Hybrids
Corresponding Author(s) : Y. Jayaprakash Rao
Asian Journal of Chemistry,
Vol. 32 No. 7 (2020): Vol 32 Issue 7
Abstract
A series of new C3-N1 directly linked chromone/1,2,3-triazole molecular hybrids synthesized by adopting low cost effective CuI catalyzed azide-alkyne 1,3-dipolar cycloaddition (Cu-AAC triazole annulation) from chromone-3-aldehyde via key intermediates 3-azidochromone, synthesized from another intermediate 3-hydroxychromone. These synthetic 1,2,3-triazole embedded chromones are the new addition to the click chemistry family. The structures of final products established by IR, NMR and mass spectral analysis.
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- L. Rackova, S. Firakova, D. Kostalova, M. Stefek, E. Sturdik and M. Majekova, Bioorg. Med. Chem., 13, 6477 (2005); https://doi.org/10.1016/j.bmc.2005.07.047
- E. Csepanyi, P. Szabados-Furjesi, A. Kiss-Szikszai, L.M. Frensemeier, U. Karst, I. Lekli, D.D. Haines, A. Tosaki and I. Bak, Molecules, 22, 588 (2017); https://doi.org/10.3390/molecules22040588
- S. Khadem and R.J. Marles, Molecules, 17, 191 (2012); https://doi.org/10.3390/molecules17010191
- M.E. Hegazy, H.M.A. El-Hamd, A.M. El-Halawany, P.C. Djemgou, A.A. Shahat and P.W. Pare, J. Nat. Prod., 74, 937 (2011); https://doi.org/10.1021/np100378d
- R.S.Keri, S. Budagumpi, R.K.Pai and R.G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014); https://doi.org/10.1016/j.ejmech.2014.03.047
- M. Hanif, M. Saleem, M.T. Hussain, N.H. Rama, S. Zaib, M.A.M. Aslam, P.G. Jones and J. Iqbal, J. Braz. Chem. Soc., 23, 854 (2012); https://doi.org/10.1590/S0103-50532012000500010
- W.T. Li, W.H. Wu, C.H. Tang, R. Tai and S.T. Chen, ACS Comb. Sci., 13, 72 (2011); https://doi.org/10.1021/co1000234
- G.O. Resende, S.F. Teixeira, I.F. Figueiredo, A.A. Godoy, D.J.F. Lougon, B.A. Cotrim and F.C. de Souza, Int. J. Electrochem., 2019, 6759478 (2019); https://doi.org/10.1155/2019/6759478
- J.F. Lutz, Angew. Chem. Int. Ed., 46, 1018 (2007); https://doi.org/10.1002/anie.200604050
- D. Dheer, V. Singh and R. Shankar, Bioorg. Chem., 71, 30 (2017); https://doi.org/10.1016/j.bioorg.2017.01.010
- V. Pervaram, D. Ashok, C.V.R. Reddy, M. Sarasija and A. Rao, Russ. J. Gen. Chem., 88, 566 (2018); https://doi.org/10.1134/S1070363218030283
- T. Sowjanya, Y.J. Rao and N.Y.S. Murthy, Russ. J. Gen. Chem., 87, 1864 (2017); https://doi.org/10.1134/S1070363217080357
- Y.J. Rao, T. Sowjanya, G. Thirupathi, N.Y.S. Murthy and K.S. Sravant, Mol. Divers., 22, 803 (2018); https://doi.org/10.1007/s11030-018-9833-4
- M.K. Reddy, Y.J. Rao and G.L.D. Krupadanam, J. Saudi Chem. Soc., 19, 372 (2015); https://doi.org/10.1016/j.jscs.2012.04.006
- G. Madhu, M. Sudhakar, K.S. Kumar, G.R. Reddy, K. Ramakrishna, A. Sravani and Ch. Prasad Rao, Russ. J. Gen. Chem., 87, 2421 (2017); https://doi.org/10.1134/S1070363217100243
- V. Satyanarayana, C.P. Rao, G.L.D. Krupadanam and G. Srimannarayana, Synth. Commun., 21, 1455 (1991); https://doi.org/10.1080/00397919108016418
- Y.J. Rao, E.Y. Goud, Y. Hemasri, N. Jain and S. Gabriella, Russ. J. Gen. Chem., 86, 184 (2016); https://doi.org/10.1134/S1070363216010291
References
L. Rackova, S. Firakova, D. Kostalova, M. Stefek, E. Sturdik and M. Majekova, Bioorg. Med. Chem., 13, 6477 (2005); https://doi.org/10.1016/j.bmc.2005.07.047
E. Csepanyi, P. Szabados-Furjesi, A. Kiss-Szikszai, L.M. Frensemeier, U. Karst, I. Lekli, D.D. Haines, A. Tosaki and I. Bak, Molecules, 22, 588 (2017); https://doi.org/10.3390/molecules22040588
S. Khadem and R.J. Marles, Molecules, 17, 191 (2012); https://doi.org/10.3390/molecules17010191
M.E. Hegazy, H.M.A. El-Hamd, A.M. El-Halawany, P.C. Djemgou, A.A. Shahat and P.W. Pare, J. Nat. Prod., 74, 937 (2011); https://doi.org/10.1021/np100378d
R.S.Keri, S. Budagumpi, R.K.Pai and R.G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014); https://doi.org/10.1016/j.ejmech.2014.03.047
M. Hanif, M. Saleem, M.T. Hussain, N.H. Rama, S. Zaib, M.A.M. Aslam, P.G. Jones and J. Iqbal, J. Braz. Chem. Soc., 23, 854 (2012); https://doi.org/10.1590/S0103-50532012000500010
W.T. Li, W.H. Wu, C.H. Tang, R. Tai and S.T. Chen, ACS Comb. Sci., 13, 72 (2011); https://doi.org/10.1021/co1000234
G.O. Resende, S.F. Teixeira, I.F. Figueiredo, A.A. Godoy, D.J.F. Lougon, B.A. Cotrim and F.C. de Souza, Int. J. Electrochem., 2019, 6759478 (2019); https://doi.org/10.1155/2019/6759478
J.F. Lutz, Angew. Chem. Int. Ed., 46, 1018 (2007); https://doi.org/10.1002/anie.200604050
D. Dheer, V. Singh and R. Shankar, Bioorg. Chem., 71, 30 (2017); https://doi.org/10.1016/j.bioorg.2017.01.010
V. Pervaram, D. Ashok, C.V.R. Reddy, M. Sarasija and A. Rao, Russ. J. Gen. Chem., 88, 566 (2018); https://doi.org/10.1134/S1070363218030283
T. Sowjanya, Y.J. Rao and N.Y.S. Murthy, Russ. J. Gen. Chem., 87, 1864 (2017); https://doi.org/10.1134/S1070363217080357
Y.J. Rao, T. Sowjanya, G. Thirupathi, N.Y.S. Murthy and K.S. Sravant, Mol. Divers., 22, 803 (2018); https://doi.org/10.1007/s11030-018-9833-4
M.K. Reddy, Y.J. Rao and G.L.D. Krupadanam, J. Saudi Chem. Soc., 19, 372 (2015); https://doi.org/10.1016/j.jscs.2012.04.006
G. Madhu, M. Sudhakar, K.S. Kumar, G.R. Reddy, K. Ramakrishna, A. Sravani and Ch. Prasad Rao, Russ. J. Gen. Chem., 87, 2421 (2017); https://doi.org/10.1134/S1070363217100243
V. Satyanarayana, C.P. Rao, G.L.D. Krupadanam and G. Srimannarayana, Synth. Commun., 21, 1455 (1991); https://doi.org/10.1080/00397919108016418
Y.J. Rao, E.Y. Goud, Y. Hemasri, N. Jain and S. Gabriella, Russ. J. Gen. Chem., 86, 184 (2016); https://doi.org/10.1134/S1070363216010291