Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient...

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Detalles Bibliográficos
Autores: Vaillard, Victoria Anahi, Buden, Maria Eugenia, Martín, Sandra Elizabeth, Rossi, Roberto Arturo
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2009
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/26110
Acceso en línea:http://hdl.handle.net/11336/26110
Access Level:acceso abierto
Palabra clave:Azaheterocycles
Intramolecular Srn1
Pyrrole
Indole
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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repository_id_str
spelling Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophilesVaillard, Victoria AnahiBuden, Maria EugeniaMartín, Sandra ElizabethRossi, Roberto ArturoAzaheterocyclesIntramolecular Srn1PyrroleIndolehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient two-step synthesis of new fused azaheterocycles derived from pyrrole, indole, and pyrazole, as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15a-b) with a base, the corresponding anion could be formed. Then, by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%).Fil: Vaillard, Victoria Anahi. 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: Martín, Sandra Elizabeth. 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: 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; ArgentinaElsevier2009-12info: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/11336/26110Vaillard, Victoria Anahi; Buden, Maria Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto Arturo; Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles; Elsevier; Tetrahedron Letters; 50; 27; 12-2009; 3829-38320040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403909008545info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2009.04.042info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:59:18Zoai:ri.conicet.gov.ar:11336/26110instacron: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:34982024-05-08 13:59:18.499CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
title Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
spellingShingle Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
Vaillard, Victoria Anahi
Azaheterocycles
Intramolecular Srn1
Pyrrole
Indole
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
title_full Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
title_fullStr Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
title_full_unstemmed Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
title_sort Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles
dc.creator.none.fl_str_mv Vaillard, Victoria Anahi
Buden, Maria Eugenia
Martín, Sandra Elizabeth
Rossi, Roberto Arturo
author Vaillard, Victoria Anahi
author_facet Vaillard, Victoria Anahi
Buden, Maria Eugenia
Martín, Sandra Elizabeth
Rossi, Roberto Arturo
author_role author
author2 Buden, Maria Eugenia
Martín, Sandra Elizabeth
Rossi, Roberto Arturo
author2_role author
author
author
dc.subject.none.fl_str_mv Azaheterocycles
Intramolecular Srn1
Pyrrole
Indole
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Azaheterocycles
Intramolecular Srn1
Pyrrole
Indole
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description The synthesis of pyrrole, indole, and pyrazole fused azaheterocycles is presented. The anions of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under photostimulation by an intramolecular SRN1 process to yield fused azaheterocycles with good to excellent yields. We report on an efficient two-step synthesis of new fused azaheterocycles derived from pyrrole, indole, and pyrazole, as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15a-b) with a base, the corresponding anion could be formed. Then, by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%).
publishDate 2009
dc.date.none.fl_str_mv 2009-12
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/11336/26110
Vaillard, Victoria Anahi; Buden, Maria Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto Arturo; Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles; Elsevier; Tetrahedron Letters; 50; 27; 12-2009; 3829-3832
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/26110
identifier_str_mv Vaillard, Victoria Anahi; Buden, Maria Eugenia; Martín, Sandra Elizabeth; Rossi, Roberto Arturo; Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles; Elsevier; Tetrahedron Letters; 50; 27; 12-2009; 3829-3832
0040-4039
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://www.sciencedirect.com/science/article/pii/S0040403909008545
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2009.04.042
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 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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,81155

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