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

Szostak Michal | Zendy; Sautier Brice | Zendy; Spain Malcolm | Zendy; Behlendorf Maike | Zendy; Procter David J. | Zendy

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

Author(s) -

Szostak Michal,

Sautier Brice,

Spain Malcolm,

Behlendorf Maike,

Procter David J.

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201306484

Subject(s) - hemiaminal , barbituric acid , chemistry , adduct , reactivity (psychology) , bicyclic molecule , stereochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , medicine , alternative medicine , pathology

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.

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