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Kurz T, Widyan K. O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Org Biomol Chem. 2004;2(14):2023-7doi: 10.1039/b404950k.
Kurz, T., & Widyan, K. (2004). O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Organic & biomolecular chemistry, 2(14), 2023-7. https://doi.org/10.1039/b404950k
Kurz, Thomas, and Widyan, Khalid. "O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids." Organic & biomolecular chemistry vol. 2,14 (2004): 2023-7. doi: https://doi.org/10.1039/b404950k
Kurz T, Widyan K. O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Org Biomol Chem. 2004 Jul 21;2(14):2023-7. doi: 10.1039/b404950k. Epub 2004 Jun 21. PMID: 15254629.
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Org Biomol Chem. 2004 Jul 21;2(14):2023-7. doi: 10.1039/b404950k. Epub 2004 Jun 21.

O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids.

Organic & biomolecular chemistry

Thomas Kurz, Khalid Widyan

Affiliations

  1. Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany. [email protected]

PMID: 15254629 DOI: 10.1039/b404950k

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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