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Synthesis 2010(6): 943-946
DOI: 10.1055/s-0029-1218642
DOI: 10.1055/s-0029-1218642
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
New Simple Synthesis of N-Substituted 1,3-Oxazinan-2-ones
Further Information
Received
19 October 2009
Publication Date:
12 January 2010 (online)
Publication History
Publication Date:
12 January 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201006/lookinside/thumbnails/10.1055-s-0029-1218642-1.jpg)
Abstract
An efficient and simple synthesis of N-substituted 1,3-oxazinan-2-ones was developed that involves a three-component, one-pot reaction of readily available tetraethylammonium bicarbonate, 1,3-dibromopropane, and a primary amine in methanol at room temperature. l-Alanine can be used as the amino component to give the chiral product (2S)-2-(2-oxo-1,3-oxazinan-3-yl)propanoic acid.
Key words
cyclizations - urethanes - oxazinanones - amines
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References
Crystallographic data for compound 3k have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 736836; copies can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or email: deposit@ccdc.cam.ac. uk].