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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Current Organic Chemistry
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:
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.
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Piperno Anna, Scala Angela, Risitano Francesco and Grassi Giovanni, Oxazol-5-(4H)-Ones. Part 1. Synthesis and Reactivity as 1,3-dipoles, Current Organic Chemistry 2014; 18 (21) . https://dx.doi.org/10.2174/1385272819666140915213429
DOI https://dx.doi.org/10.2174/1385272819666140915213429 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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