Oxazol-5-(4H)-Ones. Part 1. Synthesis and Reactivity as 1,3-dipoles

Author(s): Anna Piperno, Angela Scala, Francesco Risitano, Giovanni Grassi

Journal Name: Current Organic Chemistry

Volume 18 , Issue 21 , 2014


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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.

Keywords: Azlactones, enantioselective1, 3-dipolar cycloaddition, imidazoline, NF-κB inhibitors, oxazolones, proteasome inhibitors, pyrrolidine.

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Article Details

VOLUME: 18
ISSUE: 21
Year: 2014
Published on: 19 November, 2014
Page: [2691 - 2710]
Pages: 20
DOI: 10.2174/1385272819666140915213429
Price: $58

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