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Synthesis of 4-phenyltetralone derivatives and reaction mechanism

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Abstract

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 AAL1. In second step, intramolecular acylation of the intermediates4 to6, 4 can be transformed to a triflic acid-carboxylic anhydride and then the cyclization is undergone after leaving of the triflate anion.

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Authors and Affiliations

  1. College of Pharmacy, Duksung Women’s University, 419, Ssangmun-dong, Tobong-ku, 132-714, Seoul, Korea

    Soon-Kyoung Kwon & Young-Nam Park

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  1. Soon-Kyoung Kwon
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  2. Young-Nam Park
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Correspondence to Soon-Kyoung Kwon.

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Kwon, SK., Park, YN. Synthesis of 4-phenyltetralone derivatives and reaction mechanism. Arch Pharm Res 23, 329–331 (2000). https://doi.org/10.1007/BF02975442

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  • DOI: https://doi.org/10.1007/BF02975442

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