Ultrasound-Assisted Synthesis of β-enaminone Derivatives via Tin(IV)- Catalyzed Addition Reaction from β-dicarbonyl Compounds with Nitriles

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Abstract

An efficient and eco-friendly approach for the synthesis of β-enaminone derivatives is described by adding nitriles with β-dicarbonyl compounds under ultrasound irradiation conditions at room temperature. The scope and limitation of this strategy are also discussed. A variety of substituted amides can be obtained in moderate to good yields. We hope that this protocol for the efficient synthesis of β-enaminones will offer insights into further investigations.

Keywords: Tin, catalysis, β-dicarbonyl compounds, ultrasound irradiation, enaminone, synthesis.

Graphical Abstract

[1]
Hogenkamp, D.J.; Johnstone, T.B.C.; Huang, J-C.; Li, W.Y.; Tran, M.; Whittemore, E.R.; Bagnera, R.E.; Gee, K.W. J. Med. Chem., 2007, 50(14), 3369-3379.
[http://dx.doi.org/10.1021/jm070083v] [PMID: 17571865]
[2]
Bangalore, P.K.; Vagolu, S.K.; Bollikanda, R.K.; Veeragoni, D.K.; Choudante, P.C.; Misra, S.; Sriram, D.; Sridhar, B.; Kantevari, S. J. Nat. Prod., 2020, 83(1), 26-35.
[http://dx.doi.org/10.1021/acs.jnatprod.9b00475] [PMID: 31858800]
[3]
Klintworth, R.; de Koning, C.B.; Opatz, T.; Michael, J.P. J. Org. Chem., 2019, 84(17), 11025-11031.
[http://dx.doi.org/10.1021/acs.joc.9b01604] [PMID: 31392888]
[4]
Haight, A.R.; Stuk, T.L.; Allen, M.S.; Bhagavatula, L. Org. Process Res. Dev., 1999, 3(2), 94-100.
[http://dx.doi.org/10.1021/op9802071]
[5]
Tadesse, S.; Yu, M.; Mekonnen, L.B.; Lam, F.; Islam, S.; Tomu-sange, K.; Rahaman, M.H.; Noll, B.; Basnet, S.K.; Teo, T.; Al-brecht, H.; Milne, R.; Wang, S. J. Med. Chem., 2017, 60(5), 1892-1915.
[http://dx.doi.org/10.1021/acs.jmedchem.6b01670] [PMID: 28156111]
[6]
Lankri, D.; Albarghouti, G.; Mahameed, M.; Tsvelikhovsky, D. J. Org. Chem., 2017, 82(14), 7101-7113.
[http://dx.doi.org/10.1021/acs.joc.7b00516] [PMID: 28627896]
[7]
Korkmaz, E.; Zora, M. J. Org. Chem., 2020, 85(7), 4937-4950.
[http://dx.doi.org/10.1021/acs.joc.0c00109] [PMID: 32154723]
[8]
Seki, H.; Georg, G.I. J. Am. Chem. Soc., 2010, 132(44), 15512-15513.
[http://dx.doi.org/10.1021/ja107329k] [PMID: 20958040]
[9]
Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc., 2000, 122(42), 10405-10417.
[http://dx.doi.org/10.1021/ja000921+]
[10]
Sanz, P.; Mó, O.; Yañez, M.; Elguero, J. J. Phys. Chem. A, 2007, 111(18), 3585-3591.
[http://dx.doi.org/10.1021/jp067514q] [PMID: 17429952]
[11]
Ko, Y.O.; Chun, Y.S.; Park, C.L.; Kim, Y.; Shin, H.; Ahn, S.; Hong, J.; Lee, S.G. Org. Biomol. Chem., 2009, 7(6), 1132-1136.
[http://dx.doi.org/10.1039/b820324e] [PMID: 19262932]
[12]
Chun, Y.S.; Lee, K.K.; Ko, Y.O.; Shin, H.; Lee, S.G. Chem. Commun. (Camb.), 2008, 41(41), 5098-5100.
[http://dx.doi.org/10.1039/b813369g] [PMID: 18956034]
[13]
Li, L.; Babaoglu, E.; Harms, K.; Hil, G. Eur. J. Org. Chem., 2017, 4543-4547.
[http://dx.doi.org/10.1002/ejoc.201700868]
[14]
Pei, S.; Xue, C.; Hai, L.; Wu, Y. RSC Advances, 2014, 4, 38055-38058.
[http://dx.doi.org/10.1039/C4RA05100A]
[15]
Basato, M.; Faggin, E.; Tubaro, C. Polyhedron, 2009, 28(7), 1229-1234.
[http://dx.doi.org/10.1016/j.poly.2009.02.017]
[16]
Nicolini, M.; Citterio, A. Organic Preparations & Procedures, 1993, 25(2), 229-231.
[http://dx.doi.org/10.1080/00304949309457951]