Preparation of 3,3-disubstituted oxindoles by addition of malonates to 3-halo-3-oxindoles

A method for the synthesis of 3,3-disubstituted oxindole derivatives is described. This involves the base-mediated addition of malonate esters to 3-halo-3-alkyloxindoles. The addition is tolerant of a range of alkyl substituents at position 3 of the oxindole. Addition to an aryl chloro-oxindole is also described.