Nucleophilic substitution reaction of Morita-Baylis-Hillman adducts of isatin with X, S, N, and O-nucleophiles: A facile and efficient synthesis of highly functionalized tetrasubstituted alkene appended oxindoles

Abstract

The Morita-Baylis-Hillman adducts derived from isatins and maleimides have undergone a facile and efficient allylic nucleophilic substitution reaction with X, S, N, and O-nucleophiles to afford functionalized tetrasubstituted alkene appended oxindoles in very good yield. The MBH adducts and their acetates on treatment with halides, saturated and unsaturated amines, thiols, and trialkyl orthoformates afforded allyl halide, allyl amine, allyl thio-ether and allyl ether derivatives of oxindole, respectively. © 2011 Elsevier Ltd. All rights reserved.