Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.

Autores
Vázquez, Darián; Spanevello, Rolando Angel; Sarotti, Ariel Marcelo; Mangione, Maria Ines
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Diels-Alder betweennitroalkenes derived from a sugar scaffold and cyclopentadiene were examined.Depending on chemical structure of nitroalkene and polarity of solvent used,the reaction proceeded via the formation of a nitronate intermediate. Cyclicnitronates highly functionalized were obtained as chemically stable andstereochemically pure compounds. [3,3] sigmatropic shift of these onesafforded the Diels Alder cycloadducts in quantitative yield. Mechanisticaspects of reaction between nitroalkenes and cyclopentadiene has been studiedusing DFT computational methods. Nitronate derivatives are attractiveintermediates and open the way for the construction of valuable compounds withpotential applications.
Fil: Vázquez, Darián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
NITROALKENE
HETERO-DIELS-ALDER
NITRONIC ESTER
DFT CALCULATIONS
SIGMATROPIC REARRANGEMENT
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:11336/263663
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/263663
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.Vázquez, DariánSpanevello, Rolando AngelSarotti, Ariel MarceloMangione, Maria InesNITROALKENEHETERO-DIELS-ALDERNITRONIC ESTERDFT CALCULATIONSSIGMATROPIC REARRANGEMENThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Diels-Alder betweennitroalkenes derived from a sugar scaffold and cyclopentadiene were examined.Depending on chemical structure of nitroalkene and polarity of solvent used,the reaction proceeded via the formation of a nitronate intermediate. Cyclicnitronates highly functionalized were obtained as chemically stable andstereochemically pure compounds. [3,3] sigmatropic shift of these onesafforded the Diels Alder cycloadducts in quantitative yield. Mechanisticaspects of reaction between nitroalkenes and cyclopentadiene has been studiedusing DFT computational methods. Nitronate derivatives are attractiveintermediates and open the way for the construction of valuable compounds withpotential applications.Fil: Vázquez, Darián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaWiley VCH Verlag2024-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/263663Vázquez, Darián; Spanevello, Rolando Angel; Sarotti, Ariel Marcelo; Mangione, Maria Ines; Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 32; 6-2024; 1-81434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400650info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202400650info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:43:36Zoai:ri.conicet.gov.ar:11336/263663instacron: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 09:43:36.313CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
title Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
spellingShingle Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
Vázquez, Darián
NITROALKENE
HETERO-DIELS-ALDER
NITRONIC ESTER
DFT CALCULATIONS
SIGMATROPIC REARRANGEMENT
title_short Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
title_full Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
title_fullStr Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
title_full_unstemmed Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
title_sort Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.
dc.creator.none.fl_str_mv Vázquez, Darián
Spanevello, Rolando Angel
Sarotti, Ariel Marcelo
Mangione, Maria Ines
author Vázquez, Darián
author_facet Vázquez, Darián
Spanevello, Rolando Angel
Sarotti, Ariel Marcelo
Mangione, Maria Ines
author_role author
author2 Spanevello, Rolando Angel
Sarotti, Ariel Marcelo
Mangione, Maria Ines
author2_role author
author
author
dc.subject.none.fl_str_mv NITROALKENE
HETERO-DIELS-ALDER
NITRONIC ESTER
DFT CALCULATIONS
SIGMATROPIC REARRANGEMENT
topic NITROALKENE
HETERO-DIELS-ALDER
NITRONIC ESTER
DFT CALCULATIONS
SIGMATROPIC REARRANGEMENT
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Diels-Alder betweennitroalkenes derived from a sugar scaffold and cyclopentadiene were examined.Depending on chemical structure of nitroalkene and polarity of solvent used,the reaction proceeded via the formation of a nitronate intermediate. Cyclicnitronates highly functionalized were obtained as chemically stable andstereochemically pure compounds. [3,3] sigmatropic shift of these onesafforded the Diels Alder cycloadducts in quantitative yield. Mechanisticaspects of reaction between nitroalkenes and cyclopentadiene has been studiedusing DFT computational methods. Nitronate derivatives are attractiveintermediates and open the way for the construction of valuable compounds withpotential applications.
Fil: Vázquez, Darián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description Diels-Alder betweennitroalkenes derived from a sugar scaffold and cyclopentadiene were examined.Depending on chemical structure of nitroalkene and polarity of solvent used,the reaction proceeded via the formation of a nitronate intermediate. Cyclicnitronates highly functionalized were obtained as chemically stable andstereochemically pure compounds. [3,3] sigmatropic shift of these onesafforded the Diels Alder cycloadducts in quantitative yield. Mechanisticaspects of reaction between nitroalkenes and cyclopentadiene has been studiedusing DFT computational methods. Nitronate derivatives are attractiveintermediates and open the way for the construction of valuable compounds withpotential applications.
publishDate 2024
dc.date.none.fl_str_mv 2024-06
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/11336/263663
Vázquez, Darián; Spanevello, Rolando Angel; Sarotti, Ariel Marcelo; Mangione, Maria Ines; Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 32; 6-2024; 1-8
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/263663
identifier_str_mv Vázquez, Darián; Spanevello, Rolando Angel; Sarotti, Ariel Marcelo; Mangione, Maria Ines; Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway.; Wiley VCH Verlag; European Journal of Organic Chemistry; 27; 32; 6-2024; 1-8
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400650
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202400650
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
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1842268612882071552
score 13.13397

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