A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The...

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Autores principales: Gonçalves, Raoni S B, Dos Santos, Michael, Bernadat, Guillaume, Bonnet-Delpon, Danièle, Crousse, Benoit
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/PMC3869255/
https://www.ncbi.nlm.nih.gov/pubmed/24367404
http://dx.doi.org/10.3762/bjoc.9.275
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author Gonçalves, Raoni S B
Dos Santos, Michael
Bernadat, Guillaume
Bonnet-Delpon, Danièle
Crousse, Benoit
author_facet Gonçalves, Raoni S B
Dos Santos, Michael
Bernadat, Guillaume
Bonnet-Delpon, Danièle
Crousse, Benoit
author_sort Gonçalves, Raoni S B
collection PubMed
description Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH(4) and NiCl(2) to yield the corresponding trifluoromethylated γ-amino alcohols.
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spelling pubmed-38692552013-12-23 A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime Gonçalves, Raoni S B Dos Santos, Michael Bernadat, Guillaume Bonnet-Delpon, Danièle Crousse, Benoit Beilstein J Org Chem Full Research Paper Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH(4) and NiCl(2) to yield the corresponding trifluoromethylated γ-amino alcohols. Beilstein-Institut 2013-11-07 /pmc/articles/PMC3869255/ /pubmed/24367404 http://dx.doi.org/10.3762/bjoc.9.275 Text en Copyright © 2013, Gonçalves et al. 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
Gonçalves, Raoni S B
Dos Santos, Michael
Bernadat, Guillaume
Bonnet-Delpon, Danièle
Crousse, Benoit
A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title_full A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title_fullStr A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title_full_unstemmed A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title_short A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
title_sort one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869255/
https://www.ncbi.nlm.nih.gov/pubmed/24367404
http://dx.doi.org/10.3762/bjoc.9.275
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