Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles

Autores
Peisino, Lucas Ernesto; Camargo Solorzano, Gloria Patricia; Buden, Maria Eugenia; Pierini, Adriana Beatriz
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this report, we present a synthetic and mechanistic study of novel iterative double cyclization intramolecular SRN1 reactions from diamides bearing two aryl iodide moieties. This cyclization affords aromatic diazaheterocyclic compounds in good yields. Two synthetic strategies were employed for their preparation: intramolecular SRN1 and Homolytic Aromatic Substitution. The mechanism is non-trivial and we propose that radicals are intermediates. The regiochemistry was studied using computational calculations, employing the DFT method and the B3LYP functional. It was found that the distribution of products depends on the cyclization activation energies, proportion of neutral conformers, and the type of the electron transfer reaction.
Fil: Peisino, Lucas Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Camargo Solorzano, Gloria Patricia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
SYNTHESIS
ELECTRON TRANSFER
DFT METHOD
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:11336/47454
Acceder
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spelling Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocyclesPeisino, Lucas ErnestoCamargo Solorzano, Gloria PatriciaBuden, Maria EugeniaPierini, Adriana BeatrizSYNTHESISELECTRON TRANSFERDFT METHODhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this report, we present a synthetic and mechanistic study of novel iterative double cyclization intramolecular SRN1 reactions from diamides bearing two aryl iodide moieties. This cyclization affords aromatic diazaheterocyclic compounds in good yields. Two synthetic strategies were employed for their preparation: intramolecular SRN1 and Homolytic Aromatic Substitution. The mechanism is non-trivial and we propose that radicals are intermediates. The regiochemistry was studied using computational calculations, employing the DFT method and the B3LYP functional. It was found that the distribution of products depends on the cyclization activation energies, proportion of neutral conformers, and the type of the electron transfer reaction.Fil: Peisino, Lucas Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Camargo Solorzano, Gloria Patricia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaRoyal Society of Chemistry2015-04-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/47454Peisino, Lucas Ernesto; Camargo Solorzano, Gloria Patricia; Buden, Maria Eugenia; Pierini, Adriana Beatriz; Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles; Royal Society of Chemistry; RSC Advances; 5; 13-4-2015; 36374-363842046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C5RA04563K#info:eu-repo/semantics/altIdentifier/doi/10.1039/C5RA04563Kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:22:57Zoai:ri.conicet.gov.ar:11336/47454instacron: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:34982025-09-10 13:22:57.729CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
title Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
spellingShingle Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
Peisino, Lucas Ernesto
SYNTHESIS
ELECTRON TRANSFER
DFT METHOD
title_short Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
title_full Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
title_fullStr Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
title_full_unstemmed Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
title_sort Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles
dc.creator.none.fl_str_mv Peisino, Lucas Ernesto
Camargo Solorzano, Gloria Patricia
Buden, Maria Eugenia
Pierini, Adriana Beatriz
author Peisino, Lucas Ernesto
author_facet Peisino, Lucas Ernesto
Camargo Solorzano, Gloria Patricia
Buden, Maria Eugenia
Pierini, Adriana Beatriz
author_role author
author2 Camargo Solorzano, Gloria Patricia
Buden, Maria Eugenia
Pierini, Adriana Beatriz
author2_role author
author
author
dc.subject.none.fl_str_mv SYNTHESIS
ELECTRON TRANSFER
DFT METHOD
topic SYNTHESIS
ELECTRON TRANSFER
DFT METHOD
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this report, we present a synthetic and mechanistic study of novel iterative double cyclization intramolecular SRN1 reactions from diamides bearing two aryl iodide moieties. This cyclization affords aromatic diazaheterocyclic compounds in good yields. Two synthetic strategies were employed for their preparation: intramolecular SRN1 and Homolytic Aromatic Substitution. The mechanism is non-trivial and we propose that radicals are intermediates. The regiochemistry was studied using computational calculations, employing the DFT method and the B3LYP functional. It was found that the distribution of products depends on the cyclization activation energies, proportion of neutral conformers, and the type of the electron transfer reaction.
Fil: Peisino, Lucas Ernesto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Camargo Solorzano, Gloria Patricia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description In this report, we present a synthetic and mechanistic study of novel iterative double cyclization intramolecular SRN1 reactions from diamides bearing two aryl iodide moieties. This cyclization affords aromatic diazaheterocyclic compounds in good yields. Two synthetic strategies were employed for their preparation: intramolecular SRN1 and Homolytic Aromatic Substitution. The mechanism is non-trivial and we propose that radicals are intermediates. The regiochemistry was studied using computational calculations, employing the DFT method and the B3LYP functional. It was found that the distribution of products depends on the cyclization activation energies, proportion of neutral conformers, and the type of the electron transfer reaction.
publishDate 2015
dc.date.none.fl_str_mv 2015-04-13
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/11336/47454
Peisino, Lucas Ernesto; Camargo Solorzano, Gloria Patricia; Buden, Maria Eugenia; Pierini, Adriana Beatriz; Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles; Royal Society of Chemistry; RSC Advances; 5; 13-4-2015; 36374-36384
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47454
identifier_str_mv Peisino, Lucas Ernesto; Camargo Solorzano, Gloria Patricia; Buden, Maria Eugenia; Pierini, Adriana Beatriz; Iterative double cyclization reaction by SRN1 mechanism: A theoretical interpretation of the regiochemical outcome of diazaheterocycles; Royal Society of Chemistry; RSC Advances; 5; 13-4-2015; 36374-36384
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C5RA04563K#
info:eu-repo/semantics/altIdentifier/doi/10.1039/C5RA04563K
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
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 12.48226

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