Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

Meta- or para-nitro-(pentafluorosulfonyl)benzenes underwent the Davis reaction with arylacetonitriles to provide the SF(5)-containing benzisoxazoles. Good yields were obtained with arylacetonitriles containing the electron-neutral or electron-donor group, while those with the electron-acceptor group...

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Autores principales: Beier, Petr, Pastýříková, Tereza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3596107/
https://www.ncbi.nlm.nih.gov/pubmed/23502942
http://dx.doi.org/10.3762/bjoc.9.43
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author Beier, Petr
Pastýříková, Tereza
author_facet Beier, Petr
Pastýříková, Tereza
author_sort Beier, Petr
collection PubMed
description Meta- or para-nitro-(pentafluorosulfonyl)benzenes underwent the Davis reaction with arylacetonitriles to provide the SF(5)-containing benzisoxazoles. Good yields were obtained with arylacetonitriles containing the electron-neutral or electron-donor group, while those with the electron-acceptor group were found to be unreactive. Reductions of the benzisoxazoles gave ortho-aminobenzophenones in high yields. Their synthetic utility was demonstrated by condensation reactions with carbonyl compounds or amines to provide SF(5)-containing quinolines and quinazolines, respectively.
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spelling pubmed-35961072013-03-15 Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes Beier, Petr Pastýříková, Tereza Beilstein J Org Chem Full Research Paper Meta- or para-nitro-(pentafluorosulfonyl)benzenes underwent the Davis reaction with arylacetonitriles to provide the SF(5)-containing benzisoxazoles. Good yields were obtained with arylacetonitriles containing the electron-neutral or electron-donor group, while those with the electron-acceptor group were found to be unreactive. Reductions of the benzisoxazoles gave ortho-aminobenzophenones in high yields. Their synthetic utility was demonstrated by condensation reactions with carbonyl compounds or amines to provide SF(5)-containing quinolines and quinazolines, respectively. Beilstein-Institut 2013-02-21 /pmc/articles/PMC3596107/ /pubmed/23502942 http://dx.doi.org/10.3762/bjoc.9.43 Text en Copyright © 2013, Beier and Pastýříková https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Beier, Petr
Pastýříková, Tereza
Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title_full Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title_fullStr Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title_full_unstemmed Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title_short Synthesis of SF(5)-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
title_sort synthesis of sf(5)-containing benzisoxazoles, quinolines, and quinazolines by the davis reaction of nitro-(pentafluorosulfanyl)benzenes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3596107/
https://www.ncbi.nlm.nih.gov/pubmed/23502942
http://dx.doi.org/10.3762/bjoc.9.43
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