Direct Assembly of 2-Oxazolidinones by Chemical Fixation of Carbon Dioxide

The reaction of β‐ and γ‐haloamines with carbon dioxide to give pharmaceutically relevant 2‐oxazolidinones and 1,3‐dioxazin‐2‐ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expand...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-07, Vol.20 (29), p.8867-8871
Main Authors: Niemi, Teemu, Perea-Buceta, Jesus E., Fernández, Israel, Alakurtti, Sami, Rantala, Erika, Repo, Timo
Format: Article
Language:English
Subjects:
2-oxazolidones
antibiotics
Assembly
Carbon dioxide
carbon dioxide activation
carbon dioxide fixation
Catalysts
Chemistry
density functional calculations
Fixation
Mathematical analysis
Optimization
Urethanes
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Summary:The reaction of β‐ and γ‐haloamines with carbon dioxide to give pharmaceutically relevant 2‐oxazolidinones and 1,3‐dioxazin‐2‐ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations. The reaction of β‐ and γ‐haloamines with carbon dioxide to give pharmaceutically relevant cyclic urethanes was found to proceed efficiently in the presence of a base and in the absence of catalyst (see figure). After optimization of reaction conditions, the system was expanded to a variety of haloamines, even at a multigram scale. The reaction was further studied in silico by DFT calculations.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201402368