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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids
1Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany. kurz@chemie.uni-hamburg.de
Abstract:
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 alpha-hydroxyhydroxamic acids in excellent yields. Their deprotection provided a series of novel alpha-hydroxyhydroxamic acids.
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