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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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
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author Wiȩcław, Michał
Bobin, Mariusz
Kwast, Andrzej
Bujok, Robert
Wróbel, Zbigniew
Wojciechowski, Krzysztof
author_facet Wiȩcław, Michał
Bobin, Mariusz
Kwast, Andrzej
Bujok, Robert
Wróbel, Zbigniew
Wojciechowski, Krzysztof
author_sort Wiȩcław, Michał
collection PubMed
description 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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spelling pubmed-45912072015-10-06 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 Wiȩcław, Michał Bobin, Mariusz Kwast, Andrzej Bujok, Robert Wróbel, Zbigniew Wojciechowski, Krzysztof Mol Divers Full-Length Paper 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. Springer International Publishing 2015-08-11 2015 /pmc/articles/PMC4591207/ /pubmed/26260266 http://dx.doi.org/10.1007/s11030-015-9627-x Text en © The Author(s) 2015 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Full-Length Paper
Wiȩcław, Michał
Bobin, Mariusz
Kwast, Andrzej
Bujok, Robert
Wróbel, Zbigniew
Wojciechowski, Krzysztof
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Full-Length Paper
url 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
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