4.6 Article

Oxidative aromatic C-N bond formation: convenient synthesis of N-amino-3-nitrile-indoles via FeBr3-mediated intramolecular cyclization

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 10, Pages 3714-3725

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05069a

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Funding

  1. National Natural Science Foundation of China [20802048]
  2. Cultivation Foundation (B) for Young Faculty of Tianjin University [TJU-YFF-08B68]
  3. China Postdoctoral Science Foundation [200904507610]

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A variety of functionalized N-amino-3-nitrile-indole derivatives are obtained via an intramolecular hetero-cyclization of 2-aryl-3-substituted hydrazono-alkylnitriles using FeBr3 as a single electron oxidant. This approach allows the N-moiety on the side-chain to be annulated to the benzene ring during the final synthetic step via direct oxidative aromatic C-N bond formation.

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