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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

Abstract : 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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https://hal.archives-ouvertes.fr/hal-00764828
Contributor : Aurélien Lesnard <>
Submitted on : Thursday, December 13, 2012 - 2:04:03 PM
Last modification on : Wednesday, December 16, 2020 - 5:25:05 PM

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Maria Pereira, Valérie Thiéry. One-Pot Synthesis of Pyrrolo[1,2‑a]quinoxaline Derivatives via Iron-Promoted Aryl Nitro Reduction and Aerobic Oxidation of Alcohols. Organic Letters, American Chemical Society, 2012, 14, pp.4754-4757. ⟨10.1021/ol302006b⟩. ⟨hal-00764828⟩

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