Selective Reduction of Barbituric Acids Using SmI sub(2)/H sub(2)O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI sub(2)/H sub(2)O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Making a mark: Since the 1864 landmark discovery by Adolf vonBaeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-11, Vol.52 (48), p.12559-12563
Hauptverfasser: Szostak, Michal, Sautier, Brice, Spain, Malcolm, Behlendorf, Maike, Procter, David J
Format: Artikel
Sprache:eng
Schlagworte:
Adducts
Landmarks
Polarity
Reduction
Structural analysis
Synthesis
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Beschreibung
Zusammenfassung:Making a mark: Since the 1864 landmark discovery by Adolf vonBaeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal products by a general single-electron-transfer polarity reversal mechanism.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201306484