Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations

Autores
Bassaco, Mariana M.; Fortes, Margiani P.; Kaufman, Teodoro Saul; Silveira, Claudio
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A robust and efficient atom-economic one-pot synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles under base, acid and metal-free reaction conditions, is reported. The transformation conveniently takes place between 1,4-disubstituted 1,3-diynes and hydrazines in PEG-400 as an eco-friendly solvent, and involves two successive hydroaminations. The reaction was optimized for both, symmetric and non-symmetric 1,3-diyne-indole derivatives, as well as for hydrazine and substituted phenylhydrazines. The scope and limitations of the transformation were examined, observing that it is not sensitive to moisture or atmospheric oxygen, and that it tolerates a variety of functional groups. Even sterically hindered substrates afforded the expected pyrazoles in good to excellent yields, under mild conditions. A detailed reaction mechanism, which explains its regioselectivity, was also proposed.
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Materia
3,5-Disubstituted 1h- And 1-Aryl-1h-Pyrazoles
Hydroamination of Alkynes
Heterocycles
Green Chemical Procedure
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:11336/6068
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminationsBassaco, Mariana M.Fortes, Margiani P.Kaufman, Teodoro SaulSilveira, Claudio3,5-Disubstituted 1h- And 1-Aryl-1h-PyrazolesHydroamination of AlkynesHeterocyclesGreen Chemical Procedurehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A robust and efficient atom-economic one-pot synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles under base, acid and metal-free reaction conditions, is reported. The transformation conveniently takes place between 1,4-disubstituted 1,3-diynes and hydrazines in PEG-400 as an eco-friendly solvent, and involves two successive hydroaminations. The reaction was optimized for both, symmetric and non-symmetric 1,3-diyne-indole derivatives, as well as for hydrazine and substituted phenylhydrazines. The scope and limitations of the transformation were examined, observing that it is not sensitive to moisture or atmospheric oxygen, and that it tolerates a variety of functional groups. Even sterically hindered substrates afforded the expected pyrazoles in good to excellent yields, under mild conditions. A detailed reaction mechanism, which explains its regioselectivity, was also proposed.Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio. Universidade Federal de Santa Maria. Departamento de Química; BrasilRoyal Society of Chemistry2015-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6068Bassaco, Mariana M.; Fortes, Margiani P.; Kaufman, Teodoro Saul; Silveira, Claudio; Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations; Royal Society of Chemistry; RSC Advances; 5; 27; 3-2015; 21112-211242046-2069enginfo:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA16439Cinfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2015/ra/c4ra16439cinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:44Zoai:ri.conicet.gov.ar:11336/6068instacron: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:34982025-09-03 09:55:44.962CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
title Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
spellingShingle Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
Bassaco, Mariana M.
3,5-Disubstituted 1h- And 1-Aryl-1h-Pyrazoles
Hydroamination of Alkynes
Heterocycles
Green Chemical Procedure
title_short Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
title_full Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
title_fullStr Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
title_full_unstemmed Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
title_sort Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations
dc.creator.none.fl_str_mv Bassaco, Mariana M.
Fortes, Margiani P.
Kaufman, Teodoro Saul
Silveira, Claudio
author Bassaco, Mariana M.
author_facet Bassaco, Mariana M.
Fortes, Margiani P.
Kaufman, Teodoro Saul
Silveira, Claudio
author_role author
author2 Fortes, Margiani P.
Kaufman, Teodoro Saul
Silveira, Claudio
author2_role author
author
author
dc.subject.none.fl_str_mv 3,5-Disubstituted 1h- And 1-Aryl-1h-Pyrazoles
Hydroamination of Alkynes
Heterocycles
Green Chemical Procedure
topic 3,5-Disubstituted 1h- And 1-Aryl-1h-Pyrazoles
Hydroamination of Alkynes
Heterocycles
Green Chemical Procedure
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A robust and efficient atom-economic one-pot synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles under base, acid and metal-free reaction conditions, is reported. The transformation conveniently takes place between 1,4-disubstituted 1,3-diynes and hydrazines in PEG-400 as an eco-friendly solvent, and involves two successive hydroaminations. The reaction was optimized for both, symmetric and non-symmetric 1,3-diyne-indole derivatives, as well as for hydrazine and substituted phenylhydrazines. The scope and limitations of the transformation were examined, observing that it is not sensitive to moisture or atmospheric oxygen, and that it tolerates a variety of functional groups. Even sterically hindered substrates afforded the expected pyrazoles in good to excellent yields, under mild conditions. A detailed reaction mechanism, which explains its regioselectivity, was also proposed.
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio. Universidade Federal de Santa Maria. Departamento de Química; Brasil
description A robust and efficient atom-economic one-pot synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles under base, acid and metal-free reaction conditions, is reported. The transformation conveniently takes place between 1,4-disubstituted 1,3-diynes and hydrazines in PEG-400 as an eco-friendly solvent, and involves two successive hydroaminations. The reaction was optimized for both, symmetric and non-symmetric 1,3-diyne-indole derivatives, as well as for hydrazine and substituted phenylhydrazines. The scope and limitations of the transformation were examined, observing that it is not sensitive to moisture or atmospheric oxygen, and that it tolerates a variety of functional groups. Even sterically hindered substrates afforded the expected pyrazoles in good to excellent yields, under mild conditions. A detailed reaction mechanism, which explains its regioselectivity, was also proposed.
publishDate 2015
dc.date.none.fl_str_mv 2015-03
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/11336/6068
Bassaco, Mariana M.; Fortes, Margiani P.; Kaufman, Teodoro Saul; Silveira, Claudio; Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations; Royal Society of Chemistry; RSC Advances; 5; 27; 3-2015; 21112-21124
2046-2069
url http://hdl.handle.net/11336/6068
identifier_str_mv Bassaco, Mariana M.; Fortes, Margiani P.; Kaufman, Teodoro Saul; Silveira, Claudio; Metal-free synthesis of 3,5-disubstituted 1H- and 1-aryl-1H-pyrazoles from 1,3-diyne-indole derivatives employing two successive hydroaminations; Royal Society of Chemistry; RSC Advances; 5; 27; 3-2015; 21112-21124
2046-2069
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA16439C
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2015/ra/c4ra16439c
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
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
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score 13.13397

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