The Synthesis of Benzo[f]isoindole-1,3-dicarboxylates via an I2‑Induced 1,3-Dipolar Cycloaddition Reaction

An I2-induced 1,3-dipolar cycloaddition reaction has been developed for the synthesis of benzo­[f]­isoindole-1,3-dicarboxylates from quinones and N-substituted amino esters. The reaction proceeds in good to excellent yields in one step from 3 equiv of amino ester to react with the quinone structure. The utility of this transformation has been highlighted by its use for the construction of benzo­[f]­isoindole-1,3-dicarboxylates, which have been identified in natural products exhibiting important biological activities.

本研究开发了一种碘(I₂)诱导的1,3-偶极环加成反应（1,3-dipolar cycloaddition），可由醌类化合物与N-取代氨基酸酯一步合成苯并[f]异吲哚-1,3-二羧酸酯（benzo[f]isoindole-1,3-dicarboxylates）。该反应以3当量的氨基酸酯与醌类底物反应，可获得良好至优异的产率。此转化的应用价值得到凸显，其可用于构建这类苯并[f]异吲哚-1,3-二羧酸酯化合物，而此类化合物已在具有重要生物活性的天然产物中被鉴定发现。