Facile formation of N-alkyl-oxazolidin-2-ones from N-alkyl-nitroxyethylamines and carbonate anion in biphasic media

Nitration of N-alkyl ethanolamines ( 1) followed by treatment of their corresponding N-alkyl-N-(2-nitroxyethyl)amine salts ( 2) in a biphasic CH 2Cl 2/aqueous Na 2CO 3 or NaHCO 3 mixture at 25 °C gives N-alkyl-oxazolidin-2-ones ( 3). This represents a new method that allows the preparation of oxazol...

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Bibliographic Details
Published in:Tetrahedron letters 1998-11, Vol.39 (45), p.8211-8212
Main Authors: Sitzmann, Michael E., Kenar, James A., Trivedi, Nirupam J.
Format: Article
Language:English
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Summary:Nitration of N-alkyl ethanolamines ( 1) followed by treatment of their corresponding N-alkyl-N-(2-nitroxyethyl)amine salts ( 2) in a biphasic CH 2Cl 2/aqueous Na 2CO 3 or NaHCO 3 mixture at 25 °C gives N-alkyl-oxazolidin-2-ones ( 3). This represents a new method that allows the preparation of oxazolidinones at ambient temperature with the use of aqueous carbonate. Nitration of N-alkyl ethanolamines 1 to nitroxyethylamine salts 2 followed by treatment in a biphasic CH 2Cl 2/aqueous Na 2CO 3 mixture gives N-alkyl-2-oxazolidinones (3).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01877-2