This work is licensed under a Creative Commons Attribution 4.0 International License.
A Catalyst Free and Sustainable Synthesis of Quinazolinones in Glycerol as Green Solvent
Corresponding Author(s) : V.D. Tripathi
Asian Journal of Chemistry,
Vol. 35 No. 5 (2023): Vol 35 Issue 5, 2023
Abstract
In this article, glycerol was employed in a quest to develop an environmentally benign and sustainable synthetic protocol for synthesis of quinazolinone and spiro-quinazolinone derivatives. These studies were performed to investigate the effect of electron-rich and electronegative groups on the synthetic route of an established protocol. Different substituted isatin and benzaldehyde derivatives have been incorporated to synthesize analogues of two series of quinazolinones in order to investigate the efficacy of the developed methodology and substrate tolerance. A total of 12 derivatives were synthesized and characterized by spectroscopic techniques.
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References
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G. Sridhar, T. Gunasundari and R. Raghunathan, Tetrahedron Lett., 48, 319 (2007); https://doi.org/10.1016/j.tetlet.2006.11.002
A. Keyhani, M. Nikpassand, L.Z. Fekri and H. Kefayati, Polycycl. Arom. Compds., 42, 2607 (2022); https://doi.org/10.1080/10406638.2020.1852279
M. Delample, N. Villandier, J.-P. Douliez, S. Camy, J.-S. Condoret, Y. Pouilloux, J. Barrault and F. Jérôme, Green Chem., 12, 804 (2010); https://doi.org/10.1039/B925021B
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A. Kumar, V.D. Tripathi and P. Kumar, Green Chem., 13, 51 (2011); https://doi.org/10.1039/C0GC00523A
D. Krištofíková, V. Modrocká, M. Meciarová and R. Šebesta, ChemSusChem, 13, 2828 (2020); https://doi.org/10.1002/cssc.202000137
L.S.R. Martelli, I.V. Machado, J.R.N. dos Santos and A.G. Corrêa, Catalysts, 13, 553 (2023); https://doi.org/10.3390/catal13030553
K. Häckl and W. Kunz, Comptes Rendus Chim., 21, 572 (2018); https://doi.org/10.1016/j.crci.2018.03.010
N.S. Krishnaveni, K. Surendra, V.P. Kumar, B. Srinivas, C. Suresh Reddy and K.R. Rao, Tetrahedron Lett., 46, 4299 (2005); https://doi.org/10.1016/j.tetlet.2005.04.098
W.A. Loughlin, Aust. J. Chem., 51, 875 (1998); https://doi.org/10.1071/C98066
F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky and C. Zechel, Angew. Chem. Int. Ed. Engl., 35, 2288 (1996); https://doi.org/10.1002/anie.199622881
A. Nefzi, J.M. Ostresh and R.A. Houghten, Chem. Rev., 97, 449 (1997); https://doi.org/10.1021/cr960010b
S.M. Sondhi, N. Singh, A. Kumar, O. Lozach and L. Meijer, Bioorg. Med. Chem., 14, 3758 (2006); https://doi.org/10.1016/j.bmc.2006.01.054
J. Vinsova, K. Cermakova, A. Tomeckova, M. Ceckova, J. Jampilek, P. Cermak, J. Kunes, M. Dolezal and F. Staud, Bioorg. Med. Chem., 14, 5850 (2006); https://doi.org/10.1016/j.bmc.2006.05.030
C.E. Schiaffo, M. Rottman, S. Wittlin and P.H. Dussault, ACS Med. Chem. Lett., 2, 316 (2011); https://doi.org/10.1021/ml100308d
V. Kumar, A. Mahajan and K. Chibale, Bioorg. Med. Chem., 17, 2236 (2009); https://doi.org/10.1016/j.bmc.2008.10.072
E. Fernández-Álvaro, W.D. Hong, G.L. Nixon, P.M. O’Neill and F. Calderón, J. Med. Chem., 59, 5587 (2016); https://doi.org/10.1021/acs.jmedchem.5b01485
A. Kumar, S. Katiyar, A. Agarwal and P.M. Chauhan, Curr. Med. Chem., 10, 1137 (2003); https://doi.org/10.2174/0929867033457494
J.J. Shah and K. Mohanraj , Indian J. Pharm. Sci., 76, 46 (2014); https://doi.org/10.4103/0250-474X.128606
A. Kumar, S. Sharma, V.D. Tripathi, R.A. Maurya, S.P. Srivastava, G. Bhatia, A.K. Tamrakar and A.K. Srivastava, Bioorg. Med. Chem., 18, 4138 (2010); https://doi.org/10.1016/j.bmc.2009.11.061
H.A.M. Gomaa, Chem. Biol. Drug Des., 100, 639 (2022); https://doi.org/10.1111/cbdd.14129
A. Kumar, P. Kumar, V.D. Tripathi and S. Srivastava, RSC Adv., 2, 11641 (2012); https://doi.org/10.1039/c2ra21284f
A. Kumar, V.D. Tripathi, P. Kumar, L.P. Gupta, R. Akanksha, R. Trivedi, H. Bid, V.L. Nayak, J.A. Siddiqui, B. Chakravarti, R. Saxena, A. Dwivedi, M.I. Siddiquee, U. Siddiqui, R. Konwar and N. Chattopadhyay, Bioorg. Med. Chem., 19, 5409 (2011); https://doi.org/10.1016/j.bmc.2011.07.056
C.J. Douglas and L.E. Overman, Proc. Natl. Acad. Sci. USA, 101, 5363 (2004); https://doi.org/10.1073/pnas.0307113101
Q. Wei and L.Z. Gong, Org. Lett., 12, 1008 (2010); https://doi.org/10.1021/ol100020v
G. Pandey, P. Banerjee and S.R. Gadre, Chem. Rev., 106, 4484 (2006); https://doi.org/10.1021/cr050011g
Z.P. Wang, S. Xiang, P.L. Shao and Y. He, J. Org. Chem., 83, 10995 (2018); https://doi.org/10.1021/acs.joc.8b01622
J. Jayashankaran, R. Manian, R. Venkatesan and R. Raghunathan, Tetrahedron, 61, 5595 (2005); https://doi.org/10.1016/j.tet.2005.03.088
P. Shanmugam, B. Viswambharan, K. Selvakumar and S. Madhavan, Tetrahedron Lett., 49, 2611 (2008); https://doi.org/10.1016/j.tetlet.2008.02.104
T. Yamashita, K. Yasuda, H. Kizu, Y. Kameda, A.A. Watson, R.J. Nash, G.W.J. Fleet and N. Asano, J. Nat. Prod., 65, 1875 (2002); https://doi.org/10.1021/np020296h
C.C. Moldoveanu, P.G. Jones and L.L. Mangalagiu, Tetrahedron Lett., 50, 7205 (2009); https://doi.org/10.1016/j.tetlet.2009.10.044
J. Kobayashi, M. Tsuda, K. Agemi, H. Shigemori, M. Ishibashi, T. Sasaki and Y. Mikami, Tetrahedron, 47, 6617 (1991); https://doi.org/10.1016/S0040-4020(01)82314-0
D.M. James, H.B. Kunze and D.J. Faulkner, J. Nat. Prod., 54, 1137 (1991); https://doi.org/10.1021/np50076a040
A. Wolfson, C. Dlugy and Y. Shotland, Environ. Chem. Lett., 5, 67 (2007); https://doi.org/10.1007/s10311-006-0080-z
P. Ravichandiran and Y. Gu, Eds.: F. Jérôme and R. Luque, Glycerol as Eco-Efficient Solvent for Organic Transformations, In: Bio-based Solvents, John Wiley & Sons, Ltd, Chichester, U.K., Chap. 1, pp. 1-28 (2017).
G. Periyasami, R. Raghunathan, G. Surendiran and N. Mathivanan, Eur. J. Med. Chem., 44, 959 (2009); https://doi.org/10.1016/j.ejmech.2008.07.009