O-Protected 3-hydroxy-oxazolidin-2,4-diones: Novel precursors in the synthesis of α-hydroxyhydroxamic acids
O-Protected 3-hydroxyoxazolidin-2,4-diones have been prepared in a novel one-pot reaction by subsequent treatment of cyanohydrins with 1,1′-carbonyldiimidazole and O-protected hydroxylamines followed by acidic hydrolysis of the intermediate 4-imino-oxazolidin-2-ones. Decarbonylation of O-protected 3-hydroxyoxazolidin-2,4-diones by catalytic amounts of sodium methoxide, lithium hydroxide, sodium carbonate and caesium carbonate in methanol afforded O-protected α-hydroxyhydroxamic acids in excellent yields. Their deprotection provided a series of novel α-hydroxyhydroxamic acids.
Kurz, Thomas,Widyan, Khalid
p. 2023 - 2027
(2007/10/03)
Efficient conversion of O-substituted 3-hydroxy-4-imino-oxazolidin-2-ones into O-substituted α-hydroxyamidoximes
(Chemical equation presented) An efficient and convenient two-step synthesis of O-substituted α-hydroxyamidoximes has been developed. The first step involves a high-yielding one-pot synthesis of the so far unknown O-substituted 3-hydroxy-4-imino-oxazolidin-2-ones by reacting cyanohydrins stepwise with 1,1′-carbonyldiimidazole and O-substituted hydroxylamines. The second step represents a novel, sodium methoxide-mediated conversion of O-substituted 3-hydroxy-4-imino-oxazolidin-2-ones into the corresponding O-substituted α-hydroxyamidoximes.
Kurz, Thomas,Widyan, Khalid
p. 4403 - 4405
(2007/10/03)
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