Premium
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.