An electrochemical access to 2-amino-2,3-dihydro-1,4-benzodioxanes derived from hydroxytyrosol
作者:Anne Neudorffer、Patrick Deschamps、Martine Largeron、Brigitte Deguin
DOI:10.1039/d3ob01858j
日期:——
The anodic oxidation of a natural antioxidative catechol, hydroxytyrosol, was developed in an acetonitrile/dimethylsulfoxide (or acetonitrile/water) solvent mixture to produce in a stable way the resulting non-activated o-quinone and generate structural analogues. 2-Amino-2,3-dihydro-1,4-benzodioxane derivatives were obtained as two regioisomers in good to high overall yields (65–90%) and 1 : 3 ratios
天然抗氧化儿茶酚羟基酪醇的阳极氧化是在乙腈/二甲亚砜(或乙腈/水)溶剂混合物中开发的,以稳定的方式产生所得的非活化邻醌并产生结构类似物。通过逆电子需求 Diels-Alder (IEDDA),以良好到高的总产率 (65–90%) 和 1:3 的比例获得了两种区域异构体形式的 2-氨基-2,3-二氢-1,4-苯并二恶烷衍生物电生成的邻醌和叔烯胺之间的反应。在儿茶酚上插入吸电子(或供电子)基团改变了它们的相对比例,从而使反应变得区域特异性。与一些脂肪族烯胺发生竞争性1,6-迈克尔加成,得到2-羟基-1,2,4,5-四氢苯并[ d ]氧杂环己烷化合物。