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Synthesis 2010(6): 943-946  
DOI: 10.1055/s-0029-1218642
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Simple Synthesis of N-Substituted 1,3-Oxazinan-2-ones

Srećko Trifunovića, Dejana Dimitrijevića, Gordana Vasića, Niko Radulovićb, Mirjana Vukićevićc, Frank W. Heinemannd, Rastko D. Vukićević*a
a Department of Chemistry, Faculty of Science, University of Kragujevac, R. Domanovića 12, 34000 Kragujevac, Serbia
b Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia
c Department of Pharmacy, Medical Faculty, University of Kragujevac, S. Markovića 69, 34000 Kragujevac, Serbia
d Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nuremberg, Egerlandstr. 1, 91058 Erlangen, Germany
Fax: +381(34)335040; e-Mail: vuk@kg.ac.rs;
Further Information

Publication History

Received 19 October 2009
Publication Date:
12 January 2010 (online)

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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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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].