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Paper | Regular issue | Vol 65, No. 12, 2005, pp.2925-2935
Published online, 14th October, 2005
DOI: 10.3987/COM-05-10554
A New Synthesis of Phenolic 1-Hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines

Motoki Ikeuchi, Miyuki Ikeuchi, Kumiko Inoue, Syuhei Yamamoto, Aiko Yamauchi, and Masaru Kihara*

*Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Sho-machi, Tokushima 770-8505, Japan

Abstract

7,8-Dihydroxy-1-phenyl- and 1-(3- and 4-hydroxyphenyl)-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine derivatives (2a,b) and (3a-c) were synthesized by intramolecular Barbier reaction of N-(2-iodophenethyl)-phenacylamines (5a,b) and (12a-c) with n-C4H9Li as a key reaction step.