4.7 Article

One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 228-238

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02623

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Funding

  1. Lebanese University
  2. Chinese Scholarship Council
  3. CNRS
  4. University Paris-Sud
  5. La Ligue Contre le Cancer throughout an Equipe Labellisee 2014 grant
  6. ANR [ANR-10-LABX-33]

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A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.

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