A one-pot regiospecific synthesis of highly functionalized 1,4-benzodioxin derivatives from an electrochemically induced Diels-Alder reaction.
[reaction: see text] 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.
Xu
Daiwang
D
UMR 8638 Synthèse et Structure de Molécules d'Intérêt Pharmacologique, CNRS-Université Paris 5, 4 avenue de l'observatoire, 75270 Paris Cedex 06, France.
Chiaroni
Angèle
A
Largeron
Martine
M
D020650:Combinatorial Chemistry Techniques; D004147:Dioxins / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D015394:Molecular Structure
D004147:Dioxins