Electrochemically Promoted C−N Bond Formation from Acetylenic Amines and CO2. Synthesis of 5-Methylene-1,3-oxazolidin-2-ones

Electrochemically Promoted C−N Bond Formation from Acetylenic Amines and CO2. Synthesis of 5-Methylene-1,3-oxazolidin-2-ones

An efficient electrochemical synthesis of 5-methylene-1,3-oxazolidin-2-ones (2a−h) from acetylenic amines (1a−h) and carbon dioxide has been achieved by direct electrolysis of solution of MeCN and Et4NPF6 containing the amine, with subsequent CO2 bubbling and heating. The yields vary from good to ex...

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Veröffentlicht in:Journal of organic chemistry 2005-09, Vol.70 (19), p.7795-7798
Hauptverfasser: Feroci, Marta, Orsini, Monica, Sotgiu, Giovanni, Rossi, Leucio, Inesi, Achille
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
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Zusammenfassung:An efficient electrochemical synthesis of 5-methylene-1,3-oxazolidin-2-ones (2a−h) from acetylenic amines (1a−h) and carbon dioxide has been achieved by direct electrolysis of solution of MeCN and Et4NPF6 containing the amine, with subsequent CO2 bubbling and heating. The yields vary from good to excellent, the conditions are mild, and the use of toxic and harmful chemicals and catalysts is avoided.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0511804