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

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.

吡喃没食子酸酯的阳极氧化过程可生成化学不稳定的邻醌异二烯，这些物质通过位定向逆电子需求型迪尔斯-阿尔德反应被原地捕获于亚胺二烯体中。引入环加成反应伙伴多样性的可能性，导致了具有高达五个不同元素的富取代1,4-苯并二恶英环加成产物。该反应在温和条件下进行，具有较高的效率。该方法适用于构建与生物相关杂环库。