A simple electrochemical procedure for the N-acylation and N-alkylation of benzoxazol-2(3H)-ones has been set up via electrolysis of an ionic liquid containing a benzoxazolone followed by addition of saturated or unsaturated anhydrides or alkyl halides. The electrochemically induced N-functionalization of benzoxazol-2(3H)-ones works very well in all tested ionic liquids, avoiding the use of volatile organic solvents. The N-acyl and N-alkyl derivatives of benzoxazol-2(3H)-ones were isolated in good to excellent yields; moreover, the ionic liquid has been reused fivefold maintaining the high yield of the products.
I., C., M., F., M., O., Sotgiu, G., A., I. (2009). Electrogenerated N-heterocyclic carbenes: N-functionalization of benzoxazolones. TETRAHEDRON, 65(18), 3704-3710 [10.1016/j.tet.2009.02.057].