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A One-Pot Regiospecific Synthesis of Highly Functionalized 1,4-Benzodioxin Derivatives from an Electrochemically Induced Diels−Alder Reaction

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posted on 10.11.2005, 00:00 authored by Daiwang Xu, Angèle Chiaroni, Martine Largeron
The anodic oxidation of pyrogallol derivatives produces chemically unstable o-quinone heterodienes, which are trapped in situ by enamine dienophiles through regiospecific inverse-electron-demand Diels−Alder reactions. The possibility of introducing variations in both cycloaddition partners gives rise to highly substituted 1,4-benzodioxin cycloadducts with up to five elements of diversity. The reactions proceed under mild conditions with a good efficiency. The methodology should be amenable to the assembly of libraries of biologically relevant heterocycles.