Synthesis 2015; 47(21): 3363-3370
DOI: 10.1055/s-0034-1378788
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,3-Dihydro-1,3-oxazin-4-ones via a Mild Formal [4+2] Cycloaddition of Acylketenes with Aldimines

Yasamin Moazami
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA   eMail: jgpierce@ncsu.edu
,
Joshua G. Pierce*
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA   eMail: jgpierce@ncsu.edu
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Publikationsverlauf

Received: 02. Mai 2015

Accepted after revision: 04. Juni 2015

Publikationsdatum:
29. Juli 2015 (online)


Abstract

A mild and efficient silver-mediated synthesis of 2,3-dihydro-1,3-oxazin-4-ones through a formal [4+2] cycloaddition reaction of aldimines and acylketene intermediates is described. A variety of functionalized and potentially biologically relevant heterocycles have been accessed in moderate to high yields through this process.

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