Abstract
3-Acylmethyleneoxindoles (Ia-d) reacted with active methylene compounds (IIa-d) in EtOH, in the presence of NaOC2H5 as a catalyst at room temperature, to afford the corresponding normal Michael adducts (IIIa-f). The reactions of Ia with IIa, Ic with IIa and Id with IIa in EtOH under reflux, in the presence of Et2NH as a catalyst, produced the corresponding 2', 4'-substituted 3-(5'-amino-2'H-furan-3'-ylidene) oxindoles (IVa-c), while the reactions of Ib with IIa, Ib with IIb and Ic with IIb afforded the 2', 4'-substituted 3-(5'-amino-3'-furyl) oxindole compounds (Va-c), respectively. The Michael adducts (IIIa-c), on being refluxed in EtOH with base catalyst, gave IVa, Vb and IVb, respectively, in high yields, whereas IIId-f did not change at all. X-Ray crystallographic analyses of IVb and Vb were performed.
