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Efficient Cesium Carbonate Promoted N-Alkylations of Aromatic Cyclic Imides Under Microwave Irradiation

Mercedes Isasmendi Escudero, Lautaro D. Kremenchuzky, Isabel A. Perillo, Hugo Cerecetto, María M. Blanco*

*Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina, Email:

M. I. Escudero, L. D. Kremenchuzky, I. A. Perillo, H. Cerecetto, M. M. Blanco, Synthesis, 2011, 571-576.

DOI: 10.1055/s-0030-1258398

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An efficient and simple method enables the N-alkylation of aromatic cyclic imides using cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70˚C). The employment of microwave irradiation presents noteworthy advantages over conventional heating. The method is compatible with base labile functional groups.

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Key Words

cesium carbonate, N-alkylation of imides, microwave synthesis, nitrogen heterocycles, phthalimides, protecting groups

ID: J66-Y2011-0350