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

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journal contribution
posted on 21.09.2012, 00:00 by Maria de Fatima Pereira, Valérie Thiéry
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.