Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3‑Halo-1,2-Oxazines

In this article, comprehensive studies on the nucleophilic chlorination and bromination of readily available six-membered cyclic nitronates (1,2-oxazine-N-oxides) are reported. Under optimized conditions (POCl3 or (COBr)2 with Hünig’s base), 3-halo-substituted 1,2-oxazines, which are difficult to a...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (21), p.13794-13806
Main Authors: Malykhin, Roman S, Kokuev, Aleksandr O, Dorokhov, Valentin S, Nelyubina, Yulia V, Tartakovsky, Vladimir A, Tabolin, Andrey A, Ioffe, Sema L, Sukhorukov, Alexey Yu
Format: Article
Language:English
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Summary:In this article, comprehensive studies on the nucleophilic chlorination and bromination of readily available six-membered cyclic nitronates (1,2-oxazine-N-oxides) are reported. Under optimized conditions (POCl3 or (COBr)2 with Hünig’s base), 3-halo-substituted 1,2-oxazines, which are difficult to access by other routes, were obtained in good to high yields. The latter were shown to be convenient precursors to other 3-substituted 1,2-oxazine derivatives using Lewis/Brønsted acid-assisted substitution of the halide atom for C-, S-, and N-nucleophiles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02010