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One Pot Synthesis of 6-Phenyl-pyrazolyl-quinzolinone Derivatives using Palladium Catalyst via Suzuki-Miyaura Cross-Coupling Reaction
Corresponding Author(s) : Manickam Pramesh
Asian Journal of Chemistry,
Vol. 34 No. 4 (2022): Vol 34 Issue 4, 2022
Abstract
In present work, a palladium-mediated Suzuki-Miyaura cross-coupling reaction, which enables the efficient synthesis of 6-phenyl-pyrazolyl-quinzolinone derivatives from 6-iodo-pyrazolyl-quinzolinone, aryl boronic acid with potassium carbonate (K2CO3) is described.
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- F. Bellina, A. Carpita and R. Rossi, Synthesis, 15, 2419 (2004); https://doi.org/10.1055/s-2004-831223
- R. Martin and S.L. Buchwald, Acc. Chem. Res., 41, 1461 (2008); https://doi.org/10.1021/ar800036s
- T. Noël and S.L. Buchwald, Chem. Soc. Rev., 40, 5010 (2011); https://doi.org/10.1039/c1cs15075h
- A. Chatterjee and T.R. Ward, Catal. Lett., 146, 820 (2016); https://doi.org/10.1007/s10562-016-1707-8
- M. Ohsumi and N. Nishiwaki, ACS Omega, 2, 7767 (2017); https://doi.org/10.1021/acsomega.7b01450
- S.M. Rajesh, R.S. Kumar, L.A. Libertsen, S. Perumal, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem. Lett., 21, 3012 (2011); https://doi.org/10.1016/j.bmcl.2011.03.045
- W. Ribble, W.E. Hill, U.A. Ochsner, T.C. Jarvis, J.W. Guiles, N. Janjic and J.M. Bullard, Antimicrob. Agents Chemother., 54, 4648 (2010); https://doi.org/10.1128/AAC.00638-10
- A. Rosowsky, C.E. Mota and S.F. Queener, J. Heterocycl. Chem., 32, 335 (1995); https://doi.org/10.1002/jhet.5570320155
- E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); https://doi.org/10.1021/jm00177a025
- Z.M. Nofal, H.H. Fahmy, E.S. Zarea and W. El-Eraky, Acta Pol. Pharm., 68, 507 (2011).
- G. Nam, C.M. Yoon, E. Kim, C.K. Rhee, J.H. Kim, J.H. Shin and S.H. Kim, Bioorg. Med. Chem. Lett., 11, 611 (2001); https://doi.org/10.1016/S0960-894X(00)00681-8
- H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria and A.M. AlObaid, J. Med. Chem., 43, 2915 (2000); https://doi.org/10.1021/jm000038m
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- G. Singh, G. Singh, A.K. Yadav and A.K. Mishra, Indian J. Chem., 41B, 430 (2002).
- K.K. Liu, X. Huang, S. Bagrodia, J.H. Chen, S. Greasley, H. Cheng, S. Sun, D. Knighton, C. Rodgers, K. Rafidi, A. Zou, J. Xiao and S. Yan, Bioorg. Med. Chem. Lett., 21, 1270 (2011); https://doi.org/10.1016/j.bmcl.2010.12.026
- L.R. Bennett, C.J. Blankley, R.W. Fleming, R.D. Smith and D.K. Tessman, J. Med. Chem., 24, 382 (1981); https://doi.org/10.1021/jm00136a006
- A. Agarwal, Ramesh, Ashutosh, N. Goyal, P.M.S. Chauhan and S. Gupta, Bioorg. Med. Chem., 13, 6678 (2005); https://doi.org/10.1016/j.bmc.2005.07.043
- M.R. Mahmoud, E.A.A. El-Bordany, N.F. Hassan and F.S.M. Abu ElAzm, Phosphorus Sulfur Silicon Relat. Elem., 182, 2507 (2007); https://doi.org/10.1080/10426500701506465
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- J.I. Degraw, P.H. Christie, W.T. Colwell and F.M. Sirotnak, J. Med. Chem., 35, 320 (1992); https://doi.org/10.1021/jm00080a017
- T. Saurat, F. Buron, N. Rodrigues, M.L. de Tauzia, L. Colliandre, S. Bourg, P. Bonnet, G. Guillaumet, M. Akssira, A. Corlu, C. Guillouzo, P. Berthier, P. Rio, M.L. Jourdan, H. Benedetti and S. Routier, J. Med. Chem., 57, 613 (2014); https://doi.org/10.1021/jm401138v
- M. Fares, S.M. Abou-Seri, H.A. Abdel-Aziz, S.E. Abbas, M.M. Youssef and R.A. Eladwy, Eur. J. Med. Chem., 83, 155 (2014); https://doi.org/10.1016/j.ejmech.2014.06.027
- M. Bellam, M. Gundluru, S. Sarva, S. Chadive, V.R. Netala, V. Tartte and S.R. Cirandur, Chem. Heterocycl. Compd., 53, 173 (2017); https://doi.org/10.1007/s10593-017-2036-6
- C.R. Prakash, S. Raja, G. Saravanan, P. Dinesh Kumar and T. Panneer Selvam, Asian J. Res. Pharm. Sci., 1, 140 (2011).
References
F. Bellina, A. Carpita and R. Rossi, Synthesis, 15, 2419 (2004); https://doi.org/10.1055/s-2004-831223
R. Martin and S.L. Buchwald, Acc. Chem. Res., 41, 1461 (2008); https://doi.org/10.1021/ar800036s
T. Noël and S.L. Buchwald, Chem. Soc. Rev., 40, 5010 (2011); https://doi.org/10.1039/c1cs15075h
A. Chatterjee and T.R. Ward, Catal. Lett., 146, 820 (2016); https://doi.org/10.1007/s10562-016-1707-8
M. Ohsumi and N. Nishiwaki, ACS Omega, 2, 7767 (2017); https://doi.org/10.1021/acsomega.7b01450
S.M. Rajesh, R.S. Kumar, L.A. Libertsen, S. Perumal, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem. Lett., 21, 3012 (2011); https://doi.org/10.1016/j.bmcl.2011.03.045
W. Ribble, W.E. Hill, U.A. Ochsner, T.C. Jarvis, J.W. Guiles, N. Janjic and J.M. Bullard, Antimicrob. Agents Chemother., 54, 4648 (2010); https://doi.org/10.1128/AAC.00638-10
A. Rosowsky, C.E. Mota and S.F. Queener, J. Heterocycl. Chem., 32, 335 (1995); https://doi.org/10.1002/jhet.5570320155
E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch and C.A. Nichol, J. Med. Chem., 23, 327 (1980); https://doi.org/10.1021/jm00177a025
Z.M. Nofal, H.H. Fahmy, E.S. Zarea and W. El-Eraky, Acta Pol. Pharm., 68, 507 (2011).
G. Nam, C.M. Yoon, E. Kim, C.K. Rhee, J.H. Kim, J.H. Shin and S.H. Kim, Bioorg. Med. Chem. Lett., 11, 611 (2001); https://doi.org/10.1016/S0960-894X(00)00681-8
H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria and A.M. AlObaid, J. Med. Chem., 43, 2915 (2000); https://doi.org/10.1021/jm000038m
F. Reck, R. Alm, P. Brassil, J. Newman, B. DeJonge, C.J. Eyermann, G. Breault, J. Breen, J. Comita-Prevoir, M. Cronin, H. Davis, D. Ehmann, V. Galullo, B. Geng, T. Grebe, M. Morningstar, P. Walker, B. Hayter and S. Fisher, J. Med. Chem., 54, 7834 (2011); https://doi.org/10.1021/jm2008826
G. Singh, G. Singh, A.K. Yadav and A.K. Mishra, Indian J. Chem., 41B, 430 (2002).
K.K. Liu, X. Huang, S. Bagrodia, J.H. Chen, S. Greasley, H. Cheng, S. Sun, D. Knighton, C. Rodgers, K. Rafidi, A. Zou, J. Xiao and S. Yan, Bioorg. Med. Chem. Lett., 21, 1270 (2011); https://doi.org/10.1016/j.bmcl.2010.12.026
L.R. Bennett, C.J. Blankley, R.W. Fleming, R.D. Smith and D.K. Tessman, J. Med. Chem., 24, 382 (1981); https://doi.org/10.1021/jm00136a006
A. Agarwal, Ramesh, Ashutosh, N. Goyal, P.M.S. Chauhan and S. Gupta, Bioorg. Med. Chem., 13, 6678 (2005); https://doi.org/10.1016/j.bmc.2005.07.043
M.R. Mahmoud, E.A.A. El-Bordany, N.F. Hassan and F.S.M. Abu ElAzm, Phosphorus Sulfur Silicon Relat. Elem., 182, 2507 (2007); https://doi.org/10.1080/10426500701506465
E.C. Taylor, D.C. Palmer, T.J. George, S.R. Fletcher, C.P. Tseng, P.J. Harrington, G.P. Beardsley, D.J. Dumas, A. Rosowsky and M. Wick, J. Org. Chem., 48, 4852 (1983); https://doi.org/10.1021/jo00173a014
J.I. Degraw, P.H. Christie, W.T. Colwell and F.M. Sirotnak, J. Med. Chem., 35, 320 (1992); https://doi.org/10.1021/jm00080a017
T. Saurat, F. Buron, N. Rodrigues, M.L. de Tauzia, L. Colliandre, S. Bourg, P. Bonnet, G. Guillaumet, M. Akssira, A. Corlu, C. Guillouzo, P. Berthier, P. Rio, M.L. Jourdan, H. Benedetti and S. Routier, J. Med. Chem., 57, 613 (2014); https://doi.org/10.1021/jm401138v
M. Fares, S.M. Abou-Seri, H.A. Abdel-Aziz, S.E. Abbas, M.M. Youssef and R.A. Eladwy, Eur. J. Med. Chem., 83, 155 (2014); https://doi.org/10.1016/j.ejmech.2014.06.027
M. Bellam, M. Gundluru, S. Sarva, S. Chadive, V.R. Netala, V. Tartte and S.R. Cirandur, Chem. Heterocycl. Compd., 53, 173 (2017); https://doi.org/10.1007/s10593-017-2036-6
C.R. Prakash, S. Raja, G. Saravanan, P. Dinesh Kumar and T. Panneer Selvam, Asian J. Res. Pharm. Sci., 1, 140 (2011).