4.8 Article

One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives via Iron-Promoted Aryl Nitro Reduction and Aerobic Oxidation of Alcohols

Journal

ORGANIC LETTERS
Volume 14, Issue 18, Pages 4754-4757

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302006b

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Funding

  1. Comite 17 de la Ligue Nationale contre le Cancer
  2. CPER

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Here, we describe a new one-pot method to synthesize 4,7-substituted pyrrolo[1,2-a]quinoxalines and related heterocyles through a cascade of redox reactions/imine formation/intramolecular cyclization. This procedure tolerates readily available substituted 1-(2-nitrophenyl)pyrrole derivatives and aliphatic or benzylic alcohols as starting materials using iron powder and acidic conditions. This is the first example of constructing N-heterocycles via iron-mediated aryl nitro reduction and aerobic oxidation of alcohols in one pot.

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