ARTICLE TITLE: AlCl3-DMF reagent in the Friedel-Crafts reaction. The behaviour of omega-halogenoacid chlorides

ARTICLE AUTHOR: Poupaert-JH; Kanyonyo-M; Ucar-H; Mouithys-AM; Diouf-O; Lesieur-D

REPRINT AUTHOR: Poupaert, JH; UNIV CATHOLIQUE LOUVAIN; SCH PHARM, MED CHEM LAB, AVE EMMANUEL MOUNIER, UCL 7340; B-1200 BRUSSELS; BELGIUM

SOURCE: BULLETIN-DES-SOCIETES-CHIMIQUES-BELGES. JUL 1996; 105 (7) : 397-401

ABSTRACT:

2(3H)-benzoxazolones or 2(3H)-benzothiazolones react at 70-75 degrees C with omega-halogenoacyl chlorides in the presence the AlCl3-DMF complex to produce the expected ketones in 55-88 % yield. Treatment of a 2(3H)-benzoxazolone or 2(3H)-benzothiazolone by 4-chlorobutyryl chloride produced an alcohol derivative, presumably via an anchimeric participation of the 6-acyl carbonyl moiety.