Tetrahedron p. 1763 - 1772 (1998)
Update date:2022-09-26
Topics:
Ucar, Huseyin
Van Derpoorten, Kim
Depovere, Paul
Lesieur, Daniel
Isa, Majed
Masereel, Bernard
Delarge, Jacques
Poupaert, Jacques H.
6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.
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