Synthesis of 4-phenyltetralone derivatives and reaction mechanism.
4-(p-Chlorophenyl)tetralone (6) and 7-chloro-5-(p-chlorophenyl)tetralone (9) are key intermediates for the development of benzazepinone derivative haftens. These compounds could be synthesized from 4-phenyltetralone derivatives by triflic acid catalyzed Friedel-Crafts reaction. The reaction mechanism of Friedel-Crafts alkylation/acylation with lactones in triflic acid is presented. According to our tentative research, ring opening of protonated lactone (2) occurs in alkyl cleavage and the rate of the reaction is not dependent on concentration of triflic acid. So, alkylation of lactone in Friedel-Crafts reaction is presumed to be A(AL)1. In second step, intramolecular acylation of the intermediates 4 to 6, 4 can be transformed to a triflic acid-carboxylic anhydride and then the cyclization is undergone after leaving of the triflate anion.
Kwon
S K
SK
College of Pharmacy, Duksung Women's University, Seoul, Korea. skkwon@center.duksung.ac.kr
Park
Y N
YN
D001569:Benzodiazepines / Q000032:analysis*; D009281:Naphthalenes / Q000138:chemical synthesis*
D009281:Naphthalenes; D001569:Benzodiazepines