Abstract
We have developed an efficient and green synthesis of quinoline derivatives using L-proline under Knoevenagel condensation. L-proline was found to be an efficient catalyst for the Knoevenagel condensation of substituted 2-aminoaryl ketones 1 with the active methylene compounds 2, affording quinolone derivatives 3. The reaction has been done under conventional as well as under microwave conditions. The latter procedure has been found to be much more efficient in terms of time and yield.
Keywords: L-proline, Knoevenagel condensation, substituted 2-arylketones, active methylene compounds, microwave irradiation, quinoline derivatives.
Graphical Abstract
[http://dx.doi.org/10.1002/ejoc.200300513]
[http://dx.doi.org/10.1016/j.micromeso.2003.09.014]
b) Enders, D.; Muller, S.; Demir, A.S. Tetrahedron Lett., 1998, 29, 6437.
[http://dx.doi.org/10.1016/S0040-4039(00)82366-7]
b) Rand, L.; Swisher, V.; Cronin, C.J. J. Org. Chem., 1962, 27, 3505.
[http://dx.doi.org/10.1021/jo01057a024]
[http://dx.doi.org/10.1016/S0040-4039(00)93564-0]
b) Prajpati, D.; Lekhok, K.C.; Sandhu, J.S.; Ghosh, A.C. J. Chem. Soc. Perkin. Trans., 1996, 1, 959-960.
[http://dx.doi.org/10.1039/P19960000959]
[http://dx.doi.org/10.1016/S0040-4039(97)00180-9]
[http://dx.doi.org/10.1016/j.micromeso.2004.02.017]
b)Bennazha, J.; Zahouilly, M.; Boukhari, A.; Hol, E.A. J. Mol. Catal. Chem., 2003, 202, 247-252.
[http://dx.doi.org/10.1016/S1381-1169(03)00208-5]
[http://dx.doi.org/10.1007/978-1-349-05429-9]
[http://dx.doi.org/10.1016/S1473-3099(03)00671-6] [PMID: 12837348]
[http://dx.doi.org/10.1002/cmdc.200600010] [PMID: 16892398]
[http://dx.doi.org/10.1016/j.bmc.2009.12.060] [PMID: 20061161]
[http://dx.doi.org/10.1007/s00415-003-1146-5] [PMID: 12883918]
[http://dx.doi.org/10.1001/jama.289.21.2819]
[PMID: 20873428]
[http://dx.doi.org/10.1038/nchembio884] [PMID: 17496888]
[http://dx.doi.org/10.1016/j.bcp.2004.05.003] [PMID: 15450938]
[http://dx.doi.org/10.1016/S0223-5234(03)00061-8] [PMID: 12767604]
[http://dx.doi.org/10.1016/S0223-5234(00)01175-2] [PMID: 11137230]
[http://dx.doi.org/10.1021/jm101340q] [PMID: 21405128]
[http://dx.doi.org/10.1016/j.ultsonch.2010.07.020] [PMID: 20719553]
[http://dx.doi.org/10.1023/B:COHC.0000028623.41308.e5]
[http://dx.doi.org/10.1021/jo50015a019]
[http://dx.doi.org/10.1002/jccs.201400380]
[http://dx.doi.org/10.2174/1385272053369196]
[http://dx.doi.org/10.1039/B514635F] [PMID: 16358006]
[http://dx.doi.org/10.1016/S0040-4039(02)02499-1]
[http://dx.doi.org/10.1055/s-2003-36798]
[http://dx.doi.org/10.1002/anie.198102081]
[http://dx.doi.org/10.1016/j.tetlet.2005.08.042]
[http://dx.doi.org/10.1016/j.tet.2008.12.039]
[http://dx.doi.org/10.1016/0040-4020(95)00662-R]
b) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225.
[http://dx.doi.org/10.1016/S0040-4020(01)00906-1]
cVerma, R.S. Green Chem., 1999, 1, 43.
[http://dx.doi.org/10.1039/a808223e]
[http://dx.doi.org/10.1007/s11030-009-9138-8] [PMID: 19381851]
[http://dx.doi.org/10.1002/3527606556]
[http://dx.doi.org/10.1071/CH9951665]
[http://dx.doi.org/10.1021/ja994280y]
b) Córdova, A.; Notz, W.; Barbas, C.F., III Chem. Commun., 2002, 24, 3024-3025.
[http://dx.doi.org/10.1039/B207664K] [PMID: 12536798]
c) Chowdari, N.S.; Ramachary, D.B.; Barbas, C.F., III Synlett., 2003, 1906.
[http://dx.doi.org/10.1021/ja994280y]
b) Córdova, A.; Notz, W.; Barbas, C.F. Chem. Commun., 2002, 24, 3024-3025.
[http://dx.doi.org/10.1039/B207664K] [PMID: 12536798]
c) Chowdari, N.S.; Ramachary, D.B.; Barbas, C.F., III Synlett., 2003, 1906.
[http://dx.doi.org/10.1055/s-2006-926227]
b) Kotrusz, P.; Toma, S. ARKIVOC, 2006, (v), 100.
c) Mabry, J.; Ganem, B. Tetrahedron Lett., 2006, 47, 55.
[http://dx.doi.org/10.1016/j.tetlet.2005.10.124]
d) Chandrasekher, S. Vijeender, K.; Reddy, V. K. Tetrahedron Lett., 2005, 46, 6991.
e) Chandrasekhar, S.; Narsihmulu, C.; Reddy, N.R.K.; Sultana, S.S. Tetrahedron Lett., 2004, 45, 4581.
[http://dx.doi.org/10.1016/j.tetlet.2004.03.116]
f) Darbre, T.; Machuqueiro, M. Chem. Commun., 2003, 9, 1090-1091.
[http://dx.doi.org/10.1039/b301117h] [PMID: 12772917]
[http://dx.doi.org/10.2174/1570178611666140512215136]
[http://dx.doi.org/10.1055/s-2004-831185]