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)