摘要/Abstract

通过Barbier-Grignard型反应，在Ta₂O₅催化下，2，3-二氰基对苯二酚与溴苯和Mg在四氢呋喃中一锅反应成功制备出含氮杂环化合物1，3-二芳基或烷基-2H-异吲哚-4，7-二酮，该方法新颖、方便且高效，适用于不同芳基和烷基溴代物，最高收率达到96%.此外在一些实验结果的基础上，提出了涉及亲核加成和电子转移的可能的反应机理，利用1，3-二苯基-2H-异吲哚-4，7-二酮（3a）中的醌结构与胺偶联得到了更复杂的结构.
关键词: 异吲哚, Barbier-Grignard型反应, Ta₂O₅, 氧化偶联
A novel, convenient and efficient protocol to N-heterocyclic derivatives of 1,3-diaryl or diaklyl-2H-isoin-dole-4,7-dione has been developed via the Barbier-Grignard-type reaction. Good to excellent yields up to 96% have been achieved by performing the reaction in one pot using Ta₂O₅ as the catalyst. The protocol displays good tolerance to different aryl and alkyl bromides. Based on some experimental results, a plausible mechanism involving nucleophilic addition and electron transfer has been proposed. The quinone structure in 1,3-diphenyl-2H-isoindole-4,7-dione (3a) makes it coupling with amine to form more complicated structure.
Key words: isoindole, Barbier-Grignard reaction, Ta₂O₅, oxidative coupling


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