Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free Radical C–O Coupling with N-Hydroxy Compounds
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The reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals was disclosed. Traditionally, these substrates were considered as reactants for ionic transformations. Highly selective and efficient N-oxyl radical mediated C–O coupling of substituted barbituric or Meldrum’s acids with N-hydroxy compounds (N-hydroxyimides, hydroxamic acids, oximes, and N-hydroxybenzotriazole) was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C–O coupling was demonstrated using diacetyliminoxyl as both the oxidant (hydrogen atom acceptor) and the coupling partner.
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1968 ◽
Vol 33
(1)
◽
pp. 332-336
◽
2019 ◽
Vol 39
(6)
◽
pp. 1727
◽