New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization

Autores
Díaz, Jimena Estela; Garcia, Maria Beatriz; Orelli, Liliana Raquel
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The complete 1H and 13C NMR characterization of some representative examples of five and six-membered amidinoquinoxaline N-oxides 1 with dissymmetric aryl substituents and their methiodides 2 is reported. Compounds 1 were synthesized by ring closure of N-arylacetyl-N′-(2- nitrophenyl)alkylenediamines 3, followed by spontaneous heterocyclization. Methiodides 2 were prepared by quaternization of the parent heterocycles with methyl iodide. Complete assignment of the 1H and 13C NMR resonances of compounds 1,2 was made on the basis of the correlations observed in their HSQC, HMBC and NOESY spectra. The 1H NMR spectra of compounds 1,2 display diasterotopicity of methylenic hydrogens, indicative of molecular chirality due to the presence of a chiral axis (ONC-Ar bond). Further support for the existence of the atropisomers for compounds 1a,b is presented, on the basis of spectral and theoretical data.
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Garcia, Maria Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Materia
AMIDINOQUINOXALINE N-OXIDES
ATROPISOMERISM
HINDERED ROTATION
NITROGEN HETEROCYCLES
NMR
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:11336/112916
Acceder
id CONICETDig_c540d19010f5280acd38822b58405018
oai_identifier_str oai:ri.conicet.gov.ar:11336/112916
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterizationDíaz, Jimena EstelaGarcia, Maria BeatrizOrelli, Liliana RaquelAMIDINOQUINOXALINE N-OXIDESATROPISOMERISMHINDERED ROTATIONNITROGEN HETEROCYCLESNMRhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The complete 1H and 13C NMR characterization of some representative examples of five and six-membered amidinoquinoxaline N-oxides 1 with dissymmetric aryl substituents and their methiodides 2 is reported. Compounds 1 were synthesized by ring closure of N-arylacetyl-N′-(2- nitrophenyl)alkylenediamines 3, followed by spontaneous heterocyclization. Methiodides 2 were prepared by quaternization of the parent heterocycles with methyl iodide. Complete assignment of the 1H and 13C NMR resonances of compounds 1,2 was made on the basis of the correlations observed in their HSQC, HMBC and NOESY spectra. The 1H NMR spectra of compounds 1,2 display diasterotopicity of methylenic hydrogens, indicative of molecular chirality due to the presence of a chiral axis (ONC-Ar bond). Further support for the existence of the atropisomers for compounds 1a,b is presented, on the basis of spectral and theoretical data.Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Garcia, Maria Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaElsevier Science2010-10info: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/11336/112916Díaz, Jimena Estela; Garcia, Maria Beatriz; Orelli, Liliana Raquel; New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization; Elsevier Science; Journal of Molecular Structure; 982; 1-3; 10-2010; 50-560022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286010006496info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2010.07.050info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:03:32Zoai:ri.conicet.gov.ar:11336/112916instacron: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:34982025-10-22 12:03:33.178CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
title New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
spellingShingle New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
Díaz, Jimena Estela
AMIDINOQUINOXALINE N-OXIDES
ATROPISOMERISM
HINDERED ROTATION
NITROGEN HETEROCYCLES
NMR
title_short New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
title_full New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
title_fullStr New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
title_full_unstemmed New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
title_sort New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization
dc.creator.none.fl_str_mv Díaz, Jimena Estela
Garcia, Maria Beatriz
Orelli, Liliana Raquel
author Díaz, Jimena Estela
author_facet Díaz, Jimena Estela
Garcia, Maria Beatriz
Orelli, Liliana Raquel
author_role author
author2 Garcia, Maria Beatriz
Orelli, Liliana Raquel
author2_role author
author
dc.subject.none.fl_str_mv AMIDINOQUINOXALINE N-OXIDES
ATROPISOMERISM
HINDERED ROTATION
NITROGEN HETEROCYCLES
NMR
topic AMIDINOQUINOXALINE N-OXIDES
ATROPISOMERISM
HINDERED ROTATION
NITROGEN HETEROCYCLES
NMR
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 complete 1H and 13C NMR characterization of some representative examples of five and six-membered amidinoquinoxaline N-oxides 1 with dissymmetric aryl substituents and their methiodides 2 is reported. Compounds 1 were synthesized by ring closure of N-arylacetyl-N′-(2- nitrophenyl)alkylenediamines 3, followed by spontaneous heterocyclization. Methiodides 2 were prepared by quaternization of the parent heterocycles with methyl iodide. Complete assignment of the 1H and 13C NMR resonances of compounds 1,2 was made on the basis of the correlations observed in their HSQC, HMBC and NOESY spectra. The 1H NMR spectra of compounds 1,2 display diasterotopicity of methylenic hydrogens, indicative of molecular chirality due to the presence of a chiral axis (ONC-Ar bond). Further support for the existence of the atropisomers for compounds 1a,b is presented, on the basis of spectral and theoretical data.
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Garcia, Maria Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Orelli, Liliana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
description The complete 1H and 13C NMR characterization of some representative examples of five and six-membered amidinoquinoxaline N-oxides 1 with dissymmetric aryl substituents and their methiodides 2 is reported. Compounds 1 were synthesized by ring closure of N-arylacetyl-N′-(2- nitrophenyl)alkylenediamines 3, followed by spontaneous heterocyclization. Methiodides 2 were prepared by quaternization of the parent heterocycles with methyl iodide. Complete assignment of the 1H and 13C NMR resonances of compounds 1,2 was made on the basis of the correlations observed in their HSQC, HMBC and NOESY spectra. The 1H NMR spectra of compounds 1,2 display diasterotopicity of methylenic hydrogens, indicative of molecular chirality due to the presence of a chiral axis (ONC-Ar bond). Further support for the existence of the atropisomers for compounds 1a,b is presented, on the basis of spectral and theoretical data.
publishDate 2010
dc.date.none.fl_str_mv 2010-10
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/11336/112916
Díaz, Jimena Estela; Garcia, Maria Beatriz; Orelli, Liliana Raquel; New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization; Elsevier Science; Journal of Molecular Structure; 982; 1-3; 10-2010; 50-56
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/112916
identifier_str_mv Díaz, Jimena Estela; Garcia, Maria Beatriz; Orelli, Liliana Raquel; New atropisomers derived from amidinoquinoxaline N-oxides: Synthesis and NMR characterization; Elsevier Science; Journal of Molecular Structure; 982; 1-3; 10-2010; 50-56
0022-2860
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://www.sciencedirect.com/science/article/abs/pii/S0022286010006496
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2010.07.050
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 Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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_ 1846782378478927872
score 12.982451

Publicaciones similares