Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection

Autores
Plem, Silvana Cristina; Müller, Diana; Murguia, Marcelo Cesar
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of six pyrazoles was synthesized by Michael-type addition reaction. The molecules 5- amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl hydrazines (2a-f) using ethanol and fluorinated ethanol as solvents at reflux. An excellent regio-selectivity was found when pyrazole derivatives were formed as an exclusive product. No other regioisomer or uncyclised hydrazide was observed. Their structures were confirmed by spectroscopy data (1H, 13C, 19F, COSY (correlation spectroscopy), HSQC (heteronuclear single-quantum correlation spectroscopy) and HMBC (heteronuclear multiple-bond correlation spectroscopy); MS (mass-spectrometry). The yields ranged from good to excellent (47% - 93%) under mild reaction conditions. It would indicate a high selectivity in the one-step work procedure. These products (3a-f) and derivatives have a potential academic and industrial use as key intermediates, in special, for application in crop protection.
Fil: Plem, Silvana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Fil: Müller, Diana. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Materia
ARYL HYDRAZINE
AMINO PYRAZOLE
5-AMINO-1-ARYL-1H-PYRAZOLES-4-CARBONITRILES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/10051
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop ProtectionPlem, Silvana CristinaMüller, DianaMurguia, Marcelo CesarARYL HYDRAZINEAMINO PYRAZOLE5-AMINO-1-ARYL-1H-PYRAZOLES-4-CARBONITRILEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of six pyrazoles was synthesized by Michael-type addition reaction. The molecules 5- amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl hydrazines (2a-f) using ethanol and fluorinated ethanol as solvents at reflux. An excellent regio-selectivity was found when pyrazole derivatives were formed as an exclusive product. No other regioisomer or uncyclised hydrazide was observed. Their structures were confirmed by spectroscopy data (1H, 13C, 19F, COSY (correlation spectroscopy), HSQC (heteronuclear single-quantum correlation spectroscopy) and HMBC (heteronuclear multiple-bond correlation spectroscopy); MS (mass-spectrometry). The yields ranged from good to excellent (47% - 93%) under mild reaction conditions. It would indicate a high selectivity in the one-step work procedure. These products (3a-f) and derivatives have a potential academic and industrial use as key intermediates, in special, for application in crop protection.Fil: Plem, Silvana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; ArgentinaFil: Müller, Diana. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; ArgentinaFil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; ArgentinaScientific Research Publishing2015-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/10051Plem, Silvana Cristina; Müller, Diana; Murguia, Marcelo Cesar; Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection; Scientific Research Publishing; Advances in Chemical Engineering and Science; 5; 5-2015; 239-2612160-0406enginfo:eu-repo/semantics/altIdentifier/doi/10.4236/aces.2015.53025info:eu-repo/semantics/altIdentifier/url/http://file.scirp.org/pdf/ACES_2015063011544197.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:08:31Zoai:ri.conicet.gov.ar:11336/10051instacron: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 10:08:31.483CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
title Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
spellingShingle Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
Plem, Silvana Cristina
ARYL HYDRAZINE
AMINO PYRAZOLE
5-AMINO-1-ARYL-1H-PYRAZOLES-4-CARBONITRILES
title_short Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
title_full Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
title_fullStr Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
title_full_unstemmed Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
title_sort Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection
dc.creator.none.fl_str_mv Plem, Silvana Cristina
Müller, Diana
Murguia, Marcelo Cesar
author Plem, Silvana Cristina
author_facet Plem, Silvana Cristina
Müller, Diana
Murguia, Marcelo Cesar
author_role author
author2 Müller, Diana
Murguia, Marcelo Cesar
author2_role author
author
dc.subject.none.fl_str_mv ARYL HYDRAZINE
AMINO PYRAZOLE
5-AMINO-1-ARYL-1H-PYRAZOLES-4-CARBONITRILES
topic ARYL HYDRAZINE
AMINO PYRAZOLE
5-AMINO-1-ARYL-1H-PYRAZOLES-4-CARBONITRILES
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 series of six pyrazoles was synthesized by Michael-type addition reaction. The molecules 5- amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl hydrazines (2a-f) using ethanol and fluorinated ethanol as solvents at reflux. An excellent regio-selectivity was found when pyrazole derivatives were formed as an exclusive product. No other regioisomer or uncyclised hydrazide was observed. Their structures were confirmed by spectroscopy data (1H, 13C, 19F, COSY (correlation spectroscopy), HSQC (heteronuclear single-quantum correlation spectroscopy) and HMBC (heteronuclear multiple-bond correlation spectroscopy); MS (mass-spectrometry). The yields ranged from good to excellent (47% - 93%) under mild reaction conditions. It would indicate a high selectivity in the one-step work procedure. These products (3a-f) and derivatives have a potential academic and industrial use as key intermediates, in special, for application in crop protection.
Fil: Plem, Silvana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Fil: Müller, Diana. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química (i); Argentina. Universidad Nacional del Litoral. Facultad de Bioquímica y Ciencias Biológicas; Argentina
description A series of six pyrazoles was synthesized by Michael-type addition reaction. The molecules 5- amino-1-aryl-1H-pyrazole-4-carbonitrile (3a-f) were synthesized from (ethoxymethylene)malononitrile (1) and fluorinated and non-fluorinated aryl hydrazines (2a-f) using ethanol and fluorinated ethanol as solvents at reflux. An excellent regio-selectivity was found when pyrazole derivatives were formed as an exclusive product. No other regioisomer or uncyclised hydrazide was observed. Their structures were confirmed by spectroscopy data (1H, 13C, 19F, COSY (correlation spectroscopy), HSQC (heteronuclear single-quantum correlation spectroscopy) and HMBC (heteronuclear multiple-bond correlation spectroscopy); MS (mass-spectrometry). The yields ranged from good to excellent (47% - 93%) under mild reaction conditions. It would indicate a high selectivity in the one-step work procedure. These products (3a-f) and derivatives have a potential academic and industrial use as key intermediates, in special, for application in crop protection.
publishDate 2015
dc.date.none.fl_str_mv 2015-05
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/11336/10051
Plem, Silvana Cristina; Müller, Diana; Murguia, Marcelo Cesar; Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection; Scientific Research Publishing; Advances in Chemical Engineering and Science; 5; 5-2015; 239-261
2160-0406
url http://hdl.handle.net/11336/10051
identifier_str_mv Plem, Silvana Cristina; Müller, Diana; Murguia, Marcelo Cesar; Key Intermediates: A simple and Highly Selective Synthesis of 5-amino-1-aryl-1H-pyrazole-4-carbonitriles for Applications in the Crop Protection; Scientific Research Publishing; Advances in Chemical Engineering and Science; 5; 5-2015; 239-261
2160-0406
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.4236/aces.2015.53025
info:eu-repo/semantics/altIdentifier/url/http://file.scirp.org/pdf/ACES_2015063011544197.pdf
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Scientific Research Publishing
publisher.none.fl_str_mv Scientific Research Publishing
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_ 1842270048339623936
score 13.13397

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