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Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation: A Rapid Entry to Functionalized Oxindoles

2005; American Chemical Society; Volume: 7; Issue: 5 Linguagem: Inglês

10.1021/ol0473804

1523-7060

Rajamohan R. Poondra, Nicholas J. Turner,

Advanced Synthetic Organic Chemistry

A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide. [structure: see text]