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

Srećko Trifunović; Dejana Dimitrijević; Gordana Vasić; Niko Radulović; Mirjana Vukićević; Frank W. Heinemann; Rastko D. Vukićević

doi:10.1055/s-0029-1218642

PAPER

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

Srećko Trifunović^a, Dejana Dimitrijević^a, Gordana Vasić^a, Niko Radulović^b, Mirjana Vukićević^c, Frank W. Heinemann^d, 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;

Abstract

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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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