Untersuchung zur Regio‐ und Stereoselektivität der Reaktion von 7,8‐Dimethoxy‐1‐phenyl‐2,3,4,5‐tetrahydro‐1H‐3‐benzazepin mit Phenyloxiranen

Abstract

Reaction of Benzazepines with Phenyloxiranes The reaction between the 7,8‐dimethoxy‐1‐phenyl‐2,3,4,5‐tetrahydro‐1H‐3‐benzazepines ( ± )‐1, (1S)‐(−)− 1 und (1R)−( + )− 1 and racemic or optically active phenyloxiranes 2a–d leads to a mixture of the regioisomcric carbinoles 3a–d and 4a–d, respectively. In all cases the reaction is not stereospecific, but regiospecific with regard to the p‐phenyl substituted phenyloxiranes 2b–d. The ratio of the isomers was determined by HPLC and the structures of the regioisomers 3a and 4a were deduced from the 1H‐n.m.r. spectra. The newly synthesized carbinols proved to be strong re‐uptake in hibitors of the monoamines dopamine (DA), norepinephrine (NE) and serotonine (5‐HT).