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An Efficient Approach for the Esterification of 5-Chloroquinolin-8-ol through Steglich Reaction and their Antioxidant Applications
Corresponding Author(s) : Ayyakannu Arumugam Napoleon
Asian Journal of Chemistry,
Vol. 35 No. 6 (2023): Vol 35 Issue 6, 2023
Abstract
Esterification of organic molecules offers a critical process for chemical modifications. Among the various methodologies, Steglich conditions gave easiest and mild pathways. O-Acylation of 5-chloro-8-hydroxyquinoline with different acylating counterparts has been investigated. Among the various catalysts used, N,N-dimethylpyridin-4-amine (DMAP) in the presence of N,N′-dicyclohexyl carbodiimide (DCC) displayed a plausible synthetic approach through the application of Steglich esterification reaction for the synthesis of 5-chloroquinolin-8-yl-benzoates (3a-h) with good yields. The structures of the synthesized compounds were characterized through NMR, IR and MS spectral data. In present study, 5-chloro-8-hydroxy quinoline and its derivatives (3a-h) bearing various substituents were investigated for their antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. The findings revealed that the derivatives act as imminent candidates to be further developed as antioxidant agents.
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- S.M. Prajapati, K.D. Patel, R.H. Vekariya, S.N. Panchal and H.D. Patel, RSC Adv., 4, 24463 (2014); https://doi.org/10.1039/C4RA01814A
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References
S.M. Prajapati, K.D. Patel, R.H. Vekariya, S.N. Panchal and H.D. Patel, RSC Adv., 4, 24463 (2014); https://doi.org/10.1039/C4RA01814A
S. Srisung, T. Suksrichav, S. Prachayasi, S. Ruchirawat and V. Prachayasi, Int. J. Pharmacol., 9, 170 (2013); https://doi.org/10.3923/ijp.2013.170.175
K. Aggile, M. Alagumuthu, R.S. Mundre and A.A. Napoleon, J. Heterocycl. Chem., 55, 1669 (2018); https://doi.org/10.1002/jhet.3202
M. Akhter, R. Saha, O. Tanwar, M. Mumtaz Alam and M.S. Zaman, Med. Chem. Res., 24, 879 (2015); https://doi.org/10.1007/s00044-014-1139-1
M.R. Solanki, Asian J. Res. Chem, 15, 83 (2022); https://doi.org/10.52711/0974-4150.2022.00013
E. Kattnig and M. Albert, Org. Lett., 6, 945 (2004); https://doi.org/10.1021/ol0364935
M. Akcay, Appl. Catal. A Gen., 269, 157 (2004); https://doi.org/10.1016/j.apcata.2004.04.010
A. Sakakura, K. Kawajiri, T. Ohkubo, Y. Kosugi and K. Ishihara, J. Am. Chem. Soc., 129, 14775 (2007); https://doi.org/10.1021/ja075824w
P. Kumar, R.K. Pandey and M.S. Bodas, J. Mol. Catal. Chem., 181, 207 (2002); https://doi.org/10.1016/S1381-1169(01)00365-X
Y. Deng, F. Shi, J. Beng and K. Qiao, J. Mol. Catal. Chem., 165, 33 (2001); https://doi.org/10.1016/S1381-1169(00)00422-2
D. Sain, C. Kumari, A. Kumar, H.P. Nayek and S. Dey, Dalton Trans., 45, 9187 (2016); https://doi.org/10.1039/C6DT00941G
P. Ertl, E. Altmann and J.M. McKenna, J. Med. Chem., 63, 8408 (2020); https://doi.org/10.1021/acs.jmedchem.0c00754
H. Sharghi and M.H. Sarvari, Tetrahedron, 59, 3627 (2003); https://doi.org/10.1016/S0040-4020(03)00518-0
K. Ishihara, S. Nakagawa and A. Sakakura, J. Am. Chem. Soc., 127, 4168 (2005); https://doi.org/10.1021/ja050223v
K. Komura, A. Ozaki, N. Ieda and Y. Sugi, Synthesis, 3407 (2008); https://doi.org/10.1055/s-0028-1083175
E. Fischer and A. Speier, Darstellung der ester. In Untersuchungen aus Verschiedenen Gebieten, Springer: Berlin, Heidelberg, pp. 285-291 (1924).
A.G.M. Barrett and D.C. Braddock, Chem. Commun., 4, 351 (1997); https://doi.org/10.1039/a606484a
G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem. Int. Ed. Engl., 17, 569 (1978); https://doi.org/10.1002/anie.197805691
B. Neises and W. Steglich, Angew. Chem. Int. Ed. Engl., 17, 522 (1978); https://doi.org/10.1002/anie.197805221
H.M. Schotman, Recl. Trav. Chim. Pays Bas, 110, 319 (1991); https://doi.org/10.1002/recl.19911100704
A. Das and P. Theato, Macromolecules, 48, 8695 (2015); https://doi.org/10.1021/acs.macromol.5b02293
D. Su, Y. Wang and T. Yan, Chem. Commun., 545 (1999); https://doi.org/10.1039/a900577c
C. Moberg, Acc. Chem. Res., 49, 2736 (2016); https://doi.org/10.1021/acs.accounts.6b00396
C.E. Anson, G. Dave and G.R. Stephenson, Tetrahedron, 56, 2273 (2012); https://doi.org/10.1016/S0040-4020(99)01110-2
Y. Wang, F. Yu, X. Han, M. Li, Y. Tong, J. Ding and H. Hou, Inorg. Chem., 56, 5953 (2017); https://doi.org/10.1021/acs.inorgchem.7b00653