Easy Access to New Heterocyclic Systems:  1,4-Oxazine and Substituted 1,4-Oxazines

In the course of our investigations on the synthesis of new nitrogen heterocyclic derivatives, we were interested in the synthesis and study of new 1,4-oxazine rings. To this aim, the desired bisvinylphosphate was prepared from N-Boc morpholine-3,5-dione and was then engaged in palladium-catalyzed r...

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Veröffentlicht in:Journal of organic chemistry 2007-06, Vol.72 (13), p.4832-4836
Hauptverfasser: Claveau, Elise, Gillaizeau, Isabelle, Blu, Jérome, Bruel, Amélie, Coudert, Gérard
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Sprache:eng
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Zusammenfassung:In the course of our investigations on the synthesis of new nitrogen heterocyclic derivatives, we were interested in the synthesis and study of new 1,4-oxazine rings. To this aim, the desired bisvinylphosphate was prepared from N-Boc morpholine-3,5-dione and was then engaged in palladium-catalyzed reactions (reduction, Suzuki, and Stille cross-coupling reactions). The 1,4-oxazine and its corresponding 3,5-disubstituted derivatives were obtained in fair to good yields and were then functionalized under anionic conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070528n