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

  • Soumya Sarkara, Roland Fröhlichb, Bernhard Wünscha
  • Published 2013


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… (More)


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