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A Convenient Synthesis of 1-Benzyl-1,2,3,4-tetrahydroisoquinolines by Combined Strecker/Bruylants Reaction
Authors:Eberhard Reimann  Christian Ettmayr
Institution:(1) Department Pharmazie – Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, D-81377 München, Germany
Abstract:Summary. Strecker reaction of iodophenethylamines with phenylacetaldehydes afforded the corresponding agr-aminonitriles, which on treatment with i-propyl magnesium chloride underwent a Bruylants reaction to give the title compounds. Their structures were deduced by NMR and by an independent preparation starting from papaverine. The educts were easily available by standard procedures.
Keywords:, Alkaloids, Cyclizations, Hydrogenation, Iodination, Iodine-magnesium exchange reaction,
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