L-Arginine catalysed the Knoevenagel condensations of aromatic, heteroaromatic and α,β-unsaturated aldehydes with malononitrile and acetylacetone to afford α,β-unsaturated nitriles and ketones. The reactions were carried out at room temperature in the ionic liquid, 1-ethyl-3-methylimidazolium ethylsulfate. Moderate to excellent yields (45–100%) were achieved. The L-arginine/ionic liquid combination was successfully recycled for five runs without significant loss of activity.
CormaA., and Martın-ArandaR. M., Appl Catal A: General., 1993, 105, 271.
2.
GuisnetM., BarraultJ., BouchouleC., DuprezD., PerotG., MaurelR., and MontassierC., Heterogeneous catalysis and fine chemicals II, eds, CormaA., Martın-ArandaR.M., and SanchezF., Elsevier Science, Amsterdam, 1991, vol. 59, pp. 503–511.
3.
Martın-ArandaR.M., Ortega-CanteroE., Rojas-CervantesM. L., Vicente-RodriguezM. A., and Banares-MunozM. A., J. Chem. Technol. Biotechnol., 2005, 80, 234.
4.
TietzeL.F., and BeifussU., Comprehensive organic synthesis, Pergamon, New York, 1991, vol. 2, pp. 341–394.
5.
AyoubiS.A. E., Texier-BoulletF., and HamelinJ., Synthesis, 1994, 3, 258.
6.
ReddyT.I., and VermaR. S., Tetrahedron Lett., 1997, 38, 1721.
7.
BigiF., ChesiniL., MaggiR., and SartoriG., J. Org. Chem., 1999, 64, 1033.
8.
KantamM.L., RavindraA., ReddyC. V., SreedharB., and ChoudaryB. M., Adv. Synth. Catal., 2006, 348, 569.
9.
Lakshmi KantamM., ChoudaryB. M., Venkat ReddyCh., Koteswara RaoK., and FiguerasF., Chem. Commun., 1998, 9, 1033.
10.
RanuB.C., and JanaR., Eur. J. Org. Chem., 2006, 16, 3767.
11.
GreenB., CraneR. I., KhaidemI. S., LeightonR. S., NewazS. S., and SmyserT. E., J. Org. Chem., 1985, 50, 640.
12.
RaoP.S., and VenkataratnamR. V., Tetrahedron Lett., 1991, 32, 5821.
