Monday, October 21, 2013

Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

by Michal Szostak,* Brice Sautier, Malcolm Spain, Maike Behlendorf, David J. Procter*

Thumbnail image of graphical abstract

Making a mark: Since the 1864 landmark discovery by Adolf von Baeyer, 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.

Angewandte Chemie International Edition

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