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Paper | Regular issue | Vol 45, No. 6, 1997, pp.1121-1129
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7803
Use of the Triflamide Group for Friedel-Crafts Acylation of N-(β-Phenethyl)amino Acids to 3-Benzazepine Derivatives

Masami Kawase,* Noboru Motohashi, Masayuki Niwa, and Masakatsu Nozaki

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

Triflamides of N-(β-phenethyl)amino acids (1) were treated with P2O5 under the Friedel-Crafts acylation conditions to give the 3-benzazepines in good yields. N-(β-Phenethyl)-N-triflylvaline (1f) and phenylglycine (1g) were efficiently prepared from the corresponding N-triflylamino acids and β-phenethyl alcohol via the Mitsunobu reaction.