Title:Oxazol-5-(4H)-Ones. Part 1. Synthesis and Reactivity as 1,3-dipoles
VOLUME: 18 ISSUE: 21
Author(s):Anna Piperno, Angela Scala, Francesco Risitano and Giovanni Grassi
Affiliation:Dipartimento di Scienze Chimiche, Universita di Messina, V.le F. Stagno d'Alcontres 31, Messina, 98166, Italy.
Keywords:Azlactones, enantioselective1, 3-dipolar cycloaddition, imidazoline, NF-κB inhibitors, oxazolones, proteasome inhibitors, pyrrolidine.
Abstract:The interest in the chemistry of saturated oxazolones continues unabated in virtue of their usefulness as intermediates
in the synthesis of highly substituted heterocycles. This review attempts to present the prolific development of recent
years in this area and gives a critical and unified account of azlactones under the following headings: saturated oxazolone synthesis;
generation of cyclic azomethine ylide intermediates and relative oxazolone/imine cycloadditions and oxazolone/alkene
cycloadditions; general overview of their usefulness in the functionalization of carbon nanomaterials and in the synthesis of
pharmaceutically and biologically intriguing compounds. A particular attention is reserved to the enantioselective oxazolone cycloaddition
processes for both known synthetic approaches: chiral induction by metal catalysts and asymmetric activation by organocatalysts.
