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Ammonium Chloride Promoted One-Pot, Three-Component Mannich Reaction: An Efficient Synthesis of β-Amino Ketones and β-Amino Esters
Corresponding Author(s) : Rekha R. Joshi
Asian Journal of Chemistry,
Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022
Abstract
Ammonium chloride was found to efficiently reagent for the one pot-three component Mannich reaction between aromatic aldehyde, ketone and amine in ethanol at room temperature to furnish β-amino ketones in good to excellent yields. The said protocol was further applied for the direct synthesis of β-amino esters, which are important precursors for the synthesis of β-amino acids. This protocol is potentially applicable for the development of a clean and environment-friendly strategy for the synthesis of β-amino ketones and found applications in the synthesis of potent biologically active molecules due to its simple experimental conditions, inexpensive reagents and straight forward product isolation procedure.
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S.G. Subramaniapillai, J. Chem. Sci., 125, 467 (2013); https://doi.org/10.1007/s12039-013-0405-y
S. Bala, N. Sharma, A. Kajal, S. Kamboj and V. Saini, Int. J. Med. Chem., 2014, 191072 (2014); https://doi.org/10.1155/2014/191072
J.J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero and B. Olano, J. Org. Chem., 58, 5972 (1993); https://doi.org/10.1021/jo00074a024
D. Enders, M. Moser, G. Geibel and M. Laufer, Synthesis, 2040 (2004); https://doi.org/10.1055/s-2004-829142
M. Mukhopadhyay, B. Bhatia and J. Iqbal, Tetrahedron Lett., 38, 1083 (1997); https://doi.org/10.1016/S0040-4039(96)02474-4
K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura and K. Isono, Agric. Biol. Chem., 44, 1709 (1980); https://doi.org/10.1080/00021369.1980.10864202
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A. Flores, E. Cots, J. Bergès and K. Muñiz, Adv. Synth. Catal., 361, 1 (2019); https://doi.org/10.1002/adsc.201801478
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P. Phukan, D. Kataki and P. Chakraborty, Tetrahedron Lett., 47, 5523 (2006); https://doi.org/10.1016/j.tetlet.2006.05.136
B. Das, A.S. Kumar and B.R. Kanth, Synth. Commun., 39, 3111 (2009); https://doi.org/10.1080/00397910902730960
N. Saadatjoo, M. Golshekan, S. Shariati, P. Azizi and F. Nemati, Arab. J. Chem., 10, S735 (2017); https://doi.org/10.1016/j.arabjc.2012.11.018
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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
M. Shailaja, A. Manjula and B.V. Rao, Indian J. Chem., 49B, 482 (2010).
G. Tang, J. Yan, L. Fan, J. Xu, X. Song, L. Jiang, L. Luo and D. Yang, Sci. China Chem., 56, 490 (2013); https://doi.org/10.1007/s11426-012-4816-2
D. Bonne, M. Dekhane and J. Zhu, Org. Lett., 6, 4771 (2004); https://doi.org/10.1021/ol0479388
A. Shaabani, A. Bazgir and F. Teimouri, Tetrahedron Lett., 44, 857 (2003); https://doi.org/10.1016/S0040-4039(02)02612-6
J.W. Ralls, R.E. Lundin and G.F. Bailey, J. Org. Chem., 28, 3521 (1963); https://doi.org/10.1021/jo01047a061
D. Bonne, M. Dekhane and J. Zhu, Org. Lett., 7, 5285 (2005); https://doi.org/10.1021/ol052239w
A. Fayol and J. Zhu, Org. Lett., 6, 115 (2004); https://doi.org/10.1021/ol036167p
A. Shaabani, F. Rezazadeh and E. Soleimani, Monatsh. Chem., 139, 931 (2008); https://doi.org/10.1007/s00706-008-0872-x
A. Shaabani and M. Ameri, J. Chem. Res., 100 (1998); https://doi.org/10.1039/a701647f
N. Foroughifar, A. Mobinikhaledi, H. Moghanian, R. Mozafari and H.R.M. Esfahani, Synth. Commun., 41, 2663 (2011); https://doi.org/10.1080/00397911.2010.515340
T. Pirali, G.C. Tron, G. Masson and J. Zhu, Org. Lett., 9, 5275 (2007); https://doi.org/10.1021/ol7024372
M. Dabiri, M. Bahramnejad and M. Baghbanzadeh, Tetrahedron, 65, 9443 (2009); https://doi.org/10.1016/j.tet.2009.08.070