187409-84-3Relevant articles and documents
Application of the "fries like" rearrangement using ZnCL 2 for the synthesis of 6-acyl-2(3H)-benzothiazolones
Guenadil, Faouzi,Aichaoui, Hocine
, p. 1703 - 1708 (2003)
In this work we report another method of acylation on the 6-position of the 2(3H)-benzothiazolone ring with Fries-like rearrangement catalyzed by zinc chloride instead of aluminium chloride and 3-acyl-2(3H)-benzothiazolones derivatives as starting materia
'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones
Ucar, Huseyin,Van Derpoorten, Kim,Depovere, Paul,Lesieur, Daniel,Isa, Majed,Masereel, Bernard,Delarge, Jacques,Poupaert, Jacques H.
, p. 1763 - 1772 (2007/10/03)
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.
