'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

Autor:	Paul Depovere, M. Isa, Jacques H. Poupaert, Daniel Lesieur, Jacques Delarge, H Ucar, K. Van Derpoorten, Bernard Masereel
Rok vydání:	1998
Předmět:	Acylation chemistry.chemical_compound chemistry Stereochemistry Yield (chemistry) Organic Chemistry Drug Discovery Organic chemistry lipids (amino acids peptides and proteins) Biochemistry Acyl group Catalysis
Zdroj:	Tetrahedron. 54:1763-1772
ISSN:	0040-4020
Popis:	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)-benzoxazolone 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 heterocycle, at 165 degrees C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AlCl3 and the yield (76-90%) than other acylation methods previously described. (C) 1998 Elsevier Science Ltd. All rights reserved.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3fa16791080ccd12367e28626fc8bbc9 https://doi.org/10.1016/s0040-4020(97)10400-8 Zobrazit plný text záznamu Full Text from ScienceDirect