3,4,5,6-Tetrahydrophthalic anhydride (Acros Organics), ammonium acetate (Merck)

3,4,5,6-Tetrahydrophthalic anhydride (0.5 g, 3.29 mmol) and ammonium acetate (0.253 g, 3.29 mmol) were mixed in a beaker (100 mL). The mixture was placed in a domestic microwave oven and irradiated at 600 W power for 1 min, after which the solids had melted to a clear liquid and gas evolution was observed. Irradiation was continued for an additional 30 seconds and then the reaction mixture cooled to room temperature and the product was leached from the solid reaction mass with acetone (10 mL). Evaporation of the acetone and purification by column chromatography (ethyl acetate/petrol 1:3) gave the title product as pale yellow crystals. Yield (398 mg, 80%).

The reaction described is a simple, fast and environmentally friendly procedure to sythesize unsubstituted cyclic imides from corresponding cyclic anhydrides. For safety reason experiments should be performed in an efficient hood in order to avoid contact with vapors. Succinimide and phthalimide were synthesised according to this procedure in 80% and 91% yield, respectively.

m.p.: 173-177 ^oC, IR-ATR: 3240 (N-H), 2890-2963 (C-H), 1756, 1692 (C=O) cm^-1. ¹H-NMR (270MHz, DMSO-d6): 2.9-2.36 (4H, m), 1.68-1.74 (4H, m); ¹³C-NMR (67.80MHz, DMSO-d6): 167, 144.5, 20.29, 20.08.

H. Yousef, E. Benjamin, Heterocycles 2006, 68, 2259-2267.

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