Categories: C-N Bond Formation >
Synthesis of imides
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A convenient, efficient, and selective N-Alkylation of N-acidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. In this
manner, phthalimide, indole, benzimidazole, and succinimide can be successfully
alkylated.
Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004,
208-212.

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

Copper acetate promoted N-arylation of imides with boronic acids can be employed
as a major method for the synthesis of N3-aryl hydantoins.
H. M. Hügel, C. J. Rix, K. Fleck, Synlett, 2006,
2290-2292.
