Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions

Autores
Barolo, Silvia Maricel; Wang, You; Rossi, Roberto Arturo; Cuny, Gregory D.
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido[1,2-a]benzimidazoles via SRN1 mediated C–N bond forming reactions in moderate to excellent yields (58–94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C–C bond formation generating 7H-indolo[2,3-c]isoquinoline.
Fil: Barolo, Silvia Maricel. 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: Wang, You. Harvard Medical School; Estados Unidos
Fil: Rossi, Roberto Arturo. 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: Cuny, Gregory D.. Harvard Medical School; Estados Unidos. University Of Houston; Estados Unidos
Materia
Photo-Stimulate
Srn1
Heterocycles
Pyrido[1,2-A]Benzimidazoles
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/25432
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/25432
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactionsBarolo, Silvia MaricelWang, YouRossi, Roberto ArturoCuny, Gregory D.Photo-StimulateSrn1HeterocyclesPyrido[1,2-A]Benzimidazoleshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido[1,2-a]benzimidazoles via SRN1 mediated C–N bond forming reactions in moderate to excellent yields (58–94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C–C bond formation generating 7H-indolo[2,3-c]isoquinoline.Fil: Barolo, Silvia Maricel. 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: Wang, You. Harvard Medical School; Estados UnidosFil: Rossi, Roberto Arturo. 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: Cuny, Gregory D.. Harvard Medical School; Estados Unidos. University Of Houston; Estados UnidosElsevier2013-04info: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/11336/25432Barolo, Silvia Maricel; Wang, You; Rossi, Roberto Arturo; Cuny, Gregory D.; Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions; Elsevier; Tetrahedron; 69; 26; 4-2013; 5487-54940040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2013.04.087info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040402013006479info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:09:23Zoai:ri.conicet.gov.ar:11336/25432instacron: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 12:09:23.414CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
title Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
spellingShingle Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
Barolo, Silvia Maricel
Photo-Stimulate
Srn1
Heterocycles
Pyrido[1,2-A]Benzimidazoles
title_short Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
title_full Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
title_fullStr Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
title_full_unstemmed Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
title_sort Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
dc.creator.none.fl_str_mv Barolo, Silvia Maricel
Wang, You
Rossi, Roberto Arturo
Cuny, Gregory D.
author Barolo, Silvia Maricel
author_facet Barolo, Silvia Maricel
Wang, You
Rossi, Roberto Arturo
Cuny, Gregory D.
author_role author
author2 Wang, You
Rossi, Roberto Arturo
Cuny, Gregory D.
author2_role author
author
author
dc.subject.none.fl_str_mv Photo-Stimulate
Srn1
Heterocycles
Pyrido[1,2-A]Benzimidazoles
topic Photo-Stimulate
Srn1
Heterocycles
Pyrido[1,2-A]Benzimidazoles
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 photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido[1,2-a]benzimidazoles via SRN1 mediated C–N bond forming reactions in moderate to excellent yields (58–94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C–C bond formation generating 7H-indolo[2,3-c]isoquinoline.
Fil: Barolo, Silvia Maricel. 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: Wang, You. Harvard Medical School; Estados Unidos
Fil: Rossi, Roberto Arturo. 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: Cuny, Gregory D.. Harvard Medical School; Estados Unidos. University Of Houston; Estados Unidos
description The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido[1,2-a]benzimidazoles via SRN1 mediated C–N bond forming reactions in moderate to excellent yields (58–94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C–C bond formation generating 7H-indolo[2,3-c]isoquinoline.
publishDate 2013
dc.date.none.fl_str_mv 2013-04
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/11336/25432
Barolo, Silvia Maricel; Wang, You; Rossi, Roberto Arturo; Cuny, Gregory D.; Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions; Elsevier; Tetrahedron; 69; 26; 4-2013; 5487-5494
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/25432
identifier_str_mv Barolo, Silvia Maricel; Wang, You; Rossi, Roberto Arturo; Cuny, Gregory D.; Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions; Elsevier; Tetrahedron; 69; 26; 4-2013; 5487-5494
0040-4020
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2013.04.087
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040402013006479
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 12.982451

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