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Gold-Catalysis: Highly Efficient and Regio-Selective Carbonyl Migration in Alkynyl-Substituted Indole-3-Carboxamides Leading to Azepino[3,4-b]indol-1-ones

Authors

  • A. Stephen K. Hashmi,

    Corresponding author
    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-711-685-4205
    • Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-711-685-4205
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  • Weibo Yang,

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-711-685-4205
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  • Frank Rominger

    1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Fax: (+49)-711-685-4205
    2. Crystallographic investigation
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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.

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