Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

Decarboxylative Isomerization of N-Acyl-2-oxazolidinones to 2-Oxazolines

N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25−50 °C...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2008-04, Vol.73 (8), p.3292-3294
Hauptverfasser: May, Aaron E., Willoughby, Patrick H., Hoye, Thomas R.
Format: Artikel
Sprache:eng
Schlagworte:
Acylation
Carboxylic Acids - chemistry
Catalysis
Catalysts: preparations and properties
Chemistry
Cyclization
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Iodides - chemistry
Isomerism
Lithium - chemistry
Molecular Structure
Organic chemistry
Oxazoles - chemical synthesis
Oxazoles - chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25−50 °C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800076f