Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides

[Display omitted] •Efficient synthesis of 1,2,4-Oxadiazine-5-ones derivatives.•[3+3] Cycloaddition of in situ generated Aza-oxyallylic cations with nitrile oxides.•Easy operation, metal-free, good yields.•Broad functional group tolerance, excellent regioselelctivity. 1,2,4-Oxadiazin-5-ones were prep...

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Bibliographic Details
Published in:Tetrahedron letters 2018-05, Vol.59 (21), p.2018-2020
Main Authors: Wang, Gangqiang, Chen, Rongxing, Zhao, Sen, Yang, Liangfeng, Guo, Haibing, Sun, Shaofa, Wang, Jian, Domena, Justin, Xing, Yalan
Format: Article
Language:English
Subjects:
1,2,4-Oxadiazin-5-ones
Aza-oxyallylic cations
Cycloaddition
Nitrile oxides
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Summary:[Display omitted] •Efficient synthesis of 1,2,4-Oxadiazine-5-ones derivatives.•[3+3] Cycloaddition of in situ generated Aza-oxyallylic cations with nitrile oxides.•Easy operation, metal-free, good yields.•Broad functional group tolerance, excellent regioselelctivity. 1,2,4-Oxadiazin-5-ones were prepared via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides in good yields and excellent functional group compatibility. This efficient transformation is metal-free and is promoted by an inorganic base Cs2CO3. In addition, this reaction features simple-operation, mild conditions, and high regioselectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.04.025