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

Maria Pereira (1) , Valérie Thiéry

1 CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie

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

Mots clés: Iron; Redox reactions; Alcohols; Reaction products; Ethanol

Domaines: Chimie

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, 2012, 14, pp.4754-4757. ⟨10.1021/ol302006b⟩. ⟨hal-00764828⟩