Copyright (c) 2025 RAGAVI R, RAJESH P, VIGNESH N, SARATHA A
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Benign Lewis Acid Catalyzed Approach for Mannich Reaction: Straight Forward Synthesis of β-Amino Ketones using Simple Iron Salts as Catalyst
Corresponding Author(s) : P. Rajesh
Asian Journal of Chemistry,
Vol. 37 No. 8 (2025): Vol 37 Issue 8, 2025
Abstract
In this approach, FeCl3 was used as a moderate Lewis acid and an efficient catalyst to synthesize β-amino ketones via three-component Mannich reaction between series of substituted aromatic aldehyde, aryl amine and aryl ketones under mild conditions, where the Lewis acidic FeCl3 facilitates both C-C and C-N bond formation simultaneously without any complicated catalyst preparations. An inexpensive, readily accessible FeCl3 as an Lewis acid catalyst for synthesizing β-amino ketones through a straightforward tandem reaction in a one-pot protocol is unveiled with benefits like a short reaction time, rapid workup and good to outstanding yields under more eco-friendly conditions. This mild Lewis catalyst provides a sustainable and alternative method for obtaining synthetically necessary β-amino ketones under greener conditions. The present methodology opens the new doors for synthesizing substituted β-amino ketones and their chemical structures were verified by 1H and 13C NMR spectroscopic data. 1,3-Diphenyl-3-(phenylamino)propan-1-one (4a) was evaluated for antibacterial, antifungal, antioxidant and anticancer activities.
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A. Dandia, S. Bansal, R. Sharma, K.S. Rathore and V. Parewa, RSC Adv., 8, 30280 (2018); https://doi.org/10.1039/C8RA05203D
S. Palaniappan and B. Rajender, Adv. Synth. Catal., 352, 2507 (2010); https://doi.org/10.1002/adsc.201000346
S. Karahan and C. Tanyeli, Org. Biomol. Chem., 18, 479 (2020); https://doi.org/10.1039/C9OB02208B
M.S. Menkudle, A.V. Chakrawar, P.M. Kulkarni, W.N. Jadhav and S.R. Bhusare, Asian J. Green Chem., 4, 249 (2020); https://doi.org/10.22034/AJGC/2020.3.2
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F.K. Esfahani, D. Zareyee, A. Shokuhi and S.T. Bahrami, Appl. Organomet., 31, 3865 (2017); https://doi.org/10.1002/aoc.3865
S. Shaabani and A. Domling, Angew. Chem. Int. Ed., 57, 16266 (2018); https://doi.org/10.1002/anie.201811129
M. Mamaghani and R.H. Nia, Polycycl. Aromat. Compd., 41, 223 (2021); https://doi.org/10.1080/10406638.2019.1584576
X. Cui, Q. Li, L. Yao, Y. Ma, L. Zhang, C. Zhang and L. Zhao, J. Org. Chem., 86, 6592 (2021); https://doi.org/10.1021/acs.joc.1c00381
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M.D. Prabhakara and B. Maiti, Res. Chem. Intermed., 46, 2381 (2020); https://doi.org/10.1007/s11164-020-04096-w
P. Chauhan, S. Mahajan, U. Kaya, D. Hack and D. Enders, Adv. Synth. Catal., 357, 253 (2015); https://doi.org/10.1002/adsc.201401003
W. Wu, Y. Wang, J. Guo, L. Cai, Y. Chen, Y. Huang and Y. Peng, Chem. Commun., 56, 11235 (2020); https://doi.org/10.1039/D0CC03201H
S. Luo, Y. Peng, B. Zhang, P.G. Wang and J.P. Cheng, Curr. Org. Synth., 1, 405 (2004); https://doi.org/10.2174/1570179043366576
Y. Teo, Adv. Synth. Catal., 351, 720 (2009); https://doi.org/10.1002/adsc.200800746
A. Correa, S. Elmore and C. Bolm, Chem. Eur. J., 14, 3527 (2008); https://doi.org/10.1002/chem.200800293
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4
J. Kischel, I. Jovel, K. Mertins, A. Zapf and M. Beller, Org. Lett., 8, 19 (2006); https://doi.org/10.1021/ol0523143
J. Liu, T. He and L. Wang, Tetrahedron, 67, 3420 (2011); https://doi.org/10.1016/j.tet.2011.03.050
A. Teimouri and L. Ghorbanian, Int. J. Green Nanotechnol., 1, 1943089213507161 (2013); https://doi.org/10.1177/1943089213507161
F. Kabiri Esfahani, D. Zareyee, A. Shokuhi Rad and S. Taher-Bahrami, Appl. Organomet. Chem., 31, e3865 (2017); https://doi.org/10.1002/aoc.3865
S.V. Goswami, P.B. Thorat, A.V. Chakrawar and S.R. Bhusare, Mol. Divers., 17, 33 (2013); https://doi.org/10.1007/s11030-012-9414-x
A. Sudmant, M. Tierney, A. Gouldson and J. Bergerson, Academia Environ. Sci. Sustain., 1, 1 (2023); https://doi.org/10.20935/AcadEnvSci6141
L.S.K. Achary, P.S. Nayak, B. Barik, A. Kumar and P. Dash, Catal. Today, 348, 137 (2020); https://doi.org/10.1016/j.cattod.2019.07.050
S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, J. Saudi Chem. Soc., 19, 379 (2015); https://doi.org/10.1016/j.jscs.2012.04.008
Z. Li, X. Ma, J. Liu, X. Feng, G. Tian and A. Zhu, J. Mol. Catal. Chem., 272, 132 (2007); https://doi.org/10.1016/j.molcata.2007.03.029
C. Mukhopadhyay, A. Datta and R.J. Butcher, Tetrahedron Lett., 50, 4246 (2009); https://doi.org/10.1016/j.tetlet.2009.04.135
