4.8 Article

Trifluoroacetic Acid-Promoted Synthesis of 3-Hydroxy, 3-Amino and Spirooxindoles from α-Keto-N-Anilides

Journal

ORGANIC LETTERS
Volume 13, Issue 20, Pages 5536-5539

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202263a

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Funding

  1. ICSN
  2. CNRS (France)
  3. EPFL (Switzerland)
  4. EPFL

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Ketoanilides containing alkyl side chains were readily cyclized to 3-hydroxy-2-oxindoles or spirooxindoles by a single or double intramolecular Friedel-Crafts reaction in the presence of trifluoroacetic acid (TFA) at room temperature or at 45 degrees C. alpha-Iminocarboxamides, generated in situ from ketoamides, cyclized similarly to 3-aminooxindoles under identical conditions,

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