General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C–H acids in aprotic media promoted by combination of strong bases and silylating agents

Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text] -adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazole...

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Detalles Bibliográficos
Autores principales: Wiȩcław, Michał, Bobin, Mariusz, Kwast, Andrzej, Bujok, Robert, Wróbel, Zbigniew, Wojciechowski, Krzysztof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2015
Materias:
Full-Length Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4591207/
https://www.ncbi.nlm.nih.gov/pubmed/26260266
http://dx.doi.org/10.1007/s11030-015-9627-x
Descripción
Sumario:Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text] -adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s11030-015-9627-x) contains supplementary material, which is available to authorized users.

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