Bibliographic Information
Friedel-Crafts acylation of 2(3H)-benzoxazolone: investigation of the
role of the catalyst and microwave activation.
Liacha, Messaoud; Yous, Said; Poupaert, Jacques H.; Depreux, Patrick;
Aichaoui, Hocine. Institut de Chimie Pharmaceutique
Albert Lespagnol, Lille, Fr. Monatshefte
fuer Chemie (1999), 130(11), 1393-1397. CODEN:
MOCMB7 ISSN: 0026-9247. Journal written in
English. CAN 132:137316 AN
1999:797815 CAPLUS
Abstract
To study the scope and limitations of the use of complexed species of
AlCl3 in Friedel-Crafts reactions, we investigated the acetylation and
benzoylation of 2(3H)-benzoxazolone and 3-methyl-2(3H)-benzoxazolone
varying the amide complexing agent. We replaced DMF by
N-methylformamide, dimethylacetamide, pyrrolidinone,
N-methylpyrrolidinone, tetramethylurea, and DMSO. However, there
was no particular advantage of substituting DMF by another amide
ligand. This can probably be ascribed to the fact that the
complex formed between AlCl3 and the complexing agent becomes too
stable. Alternatively, a route using polyphosphoric acid and
microwave activation was explored. The major advantage of running
the reaction in a microwave oven was that a good yield was reached in a
rather short period of time.
Indexing -- Section 28-6 (Heterocyclic Compounds (More Than One
Hetero Atom)