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In order to synthesize enantiomerically pure tetrahydro-3-benzazepines with diverse substitution patterns, the lactams 3 were converted into thiolactams 4 upon treatment with Lawesson’s reagent. Instead of an Eschenmoser sulfide contraction a thiophene annulation reaction occurred, when the thiolactams 4 were reacted with ethyl bromoacetate. Altogether, enantiomerically pure thiopheneannulated 3-benzazepines 7 were prepared in a very short reaction sequence (five reaction steps) starting from commercially available o-phenylenediacetic acid

Unexpected Formation of Thiophene-annulated Tetrahydro-3- benzazepines by Alkylation of Thiolactams with Ethyl Bromoacetate