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Keywords:

  • acylamino migration;
  • alkynes;
  • gold;
  • heterocycles;
  • indoles

Abstract

An unprecedented rearrangement/anellation sequence allows the clean synthesis of azepino[3,4-b]indol-1-ones from readily available starting materials. Alkyne-substituted indole-3-carboxamides were prepared and converted to azepino[3,4-b]indol-1-ones by the SPhosAuNTf2 catalyst (SPhos=2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl). The new connectivity, which involves an unprecedented 3,2-shift of an acylamino group for the product formation, was proven by a crystal structure analysis.