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Synthesis 2009(23): 4068-4074  
DOI: 10.1055/s-0029-1217023
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Reactivity of 4-Aralkoxy(alkoxy)-5,6-dihydro-2H-1,3-oxazine-2-ones

Thomas Kurz*a, Mehdi Khankischpurb
a Institute of Pharmaceutical and Medicinal Chemistry, Heinrich-Heine Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany
Fax: +49(211)8113847; e-Mail: Thomas.Kurz@uni-duesseldorf.de;
b Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany
Further Information

Publication History

Received 5 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

The synthesis of previously unreported 4-aralkoxy(alkoxy)-5,6-dihydro-2H-1,3-oxazine-2-ones, as well as their transformation into various novel 4-functionalized 5,6-dihydro-2H-1,3-oxazine-2-ones and 1,3-oxazinane-2-ones is described.

Key words

β-hydroxyimidates - cyclization - nitrogen-containing heterocycles - N-nucleophiles - oxazinanes

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Crystallographic data for compounds 4f, 5c and 6f have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 726927 (4f), CCDC 726928 (5c) and CCDC 726929 (6f).