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 sat- urated 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.
“Electrogenerated N-heterocyclic carbene. N-Functionalization of benzoxazolones” / Chiarotto, Isabella; Feroci, Marta; Orsini, M; Sotgiu, G; Inesi, Achille. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:(2009), pp. 3704-3710. [10.1016/j.tet.2009.02.057]
“Electrogenerated N-heterocyclic carbene. N-Functionalization of benzoxazolones”
CHIAROTTO, Isabella;FEROCI, Marta;INESI, ACHILLE
2009
Abstract
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 sat- urated 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 documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.