Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs

Autores
Fustero, Santos; Roman, Raquel; Sanz Cervera, Juan F.; Simon Fuentes, Antonio; Cuñat, Ana; Villanova, Salvador; Murguia, Marcelo Cesar
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.
Fil: Fustero, Santos. Universidad de Valencia; España
Fil: Roman, Raquel. Universidad de Valencia; España
Fil: Sanz Cervera, Juan F.. Universidad de Valencia; España. Centro de Investigaciones Principe Felipe; España
Fil: Simon Fuentes, Antonio. Universidad de Valencia; España
Fil: Cuñat, Ana. Universidad de Valencia; España
Fil: Villanova, Salvador. Universidad de Valencia; España
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Materia
Pyrazol
Fluorinated Pyrazol
Fluorous
Tebufenpyrad
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/20497
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/20497
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad AnalogsFustero, SantosRoman, RaquelSanz Cervera, Juan F.Simon Fuentes, AntonioCuñat, AnaVillanova, SalvadorMurguia, Marcelo CesarPyrazolFluorinated PyrazolFluorousTebufenpyradhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.Fil: Fustero, Santos. Universidad de Valencia; EspañaFil: Roman, Raquel. Universidad de Valencia; EspañaFil: Sanz Cervera, Juan F.. Universidad de Valencia; España. Centro de Investigaciones Principe Felipe; EspañaFil: Simon Fuentes, Antonio. Universidad de Valencia; EspañaFil: Cuñat, Ana. Universidad de Valencia; EspañaFil: Villanova, Salvador. Universidad de Valencia; EspañaFil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaAmerican Chemical Society2008-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/20497Fustero, Santos; Roman, Raquel; Sanz Cervera, Juan F.; Simon Fuentes, Antonio; Cuñat, Ana; et al.; Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs; American Chemical Society; Journal of Organic Chemistry; 73; 9; 12-2008; 3523-35290022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo800251ginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jo800251ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:03Zoai:ri.conicet.gov.ar:11336/20497instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:39:03.664CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
title Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
spellingShingle Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
Fustero, Santos
Pyrazol
Fluorinated Pyrazol
Fluorous
Tebufenpyrad
title_short Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
title_full Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
title_fullStr Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
title_full_unstemmed Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
title_sort Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
dc.creator.none.fl_str_mv Fustero, Santos
Roman, Raquel
Sanz Cervera, Juan F.
Simon Fuentes, Antonio
Cuñat, Ana
Villanova, Salvador
Murguia, Marcelo Cesar
author Fustero, Santos
author_facet Fustero, Santos
Roman, Raquel
Sanz Cervera, Juan F.
Simon Fuentes, Antonio
Cuñat, Ana
Villanova, Salvador
Murguia, Marcelo Cesar
author_role author
author2 Roman, Raquel
Sanz Cervera, Juan F.
Simon Fuentes, Antonio
Cuñat, Ana
Villanova, Salvador
Murguia, Marcelo Cesar
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Pyrazol
Fluorinated Pyrazol
Fluorous
Tebufenpyrad
topic Pyrazol
Fluorinated Pyrazol
Fluorous
Tebufenpyrad
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.
Fil: Fustero, Santos. Universidad de Valencia; España
Fil: Roman, Raquel. Universidad de Valencia; España
Fil: Sanz Cervera, Juan F.. Universidad de Valencia; España. Centro de Investigaciones Principe Felipe; España
Fil: Simon Fuentes, Antonio. Universidad de Valencia; España
Fil: Cuñat, Ana. Universidad de Valencia; España
Fil: Villanova, Salvador. Universidad de Valencia; España
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
description The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.
publishDate 2008
dc.date.none.fl_str_mv 2008-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/20497
Fustero, Santos; Roman, Raquel; Sanz Cervera, Juan F.; Simon Fuentes, Antonio; Cuñat, Ana; et al.; Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs; American Chemical Society; Journal of Organic Chemistry; 73; 9; 12-2008; 3523-3529
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/20497
identifier_str_mv Fustero, Santos; Roman, Raquel; Sanz Cervera, Juan F.; Simon Fuentes, Antonio; Cuñat, Ana; et al.; Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs; American Chemical Society; Journal of Organic Chemistry; 73; 9; 12-2008; 3523-3529
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jo800251g
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jo800251g
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844613234705825792
score 13.070432

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