Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles

Autores
Martins, Guilherme M.; Zeni, Gilson; Back, David F.; Kaufman, Teodoro Saul; Silveira, Claudio C.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.
Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Zeni, Gilson. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Back, David F.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Materia
3h-Benzo[E]Indoles
Heterocycles
Iodocyclization
Phenylacetylenes
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:11336/6063
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6063
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indolesMartins, Guilherme M.Zeni, GilsonBack, David F.Kaufman, Teodoro SaulSilveira, Claudio C.3h-Benzo[E]IndolesHeterocyclesIodocyclizationPhenylacetyleneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria. Departamento de Qu ímica; BrasilFil: Zeni, Gilson. Universidade Federal de Santa Maria. Departamento de Qu ímica; BrasilFil: Back, David F.. Universidade Federal de Santa Maria. Departamento de Qu ímica; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Qu ímica; BrasilWiley2015-10-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6063Martins, Guilherme M.; Zeni, Gilson; Back, David F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles; Wiley; Advanced Synthesis & Catalysis (print); 357; 14-15; 12-10-2015; 3255-32611615-4150enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500275/abstractinfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201500275info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:34:46Zoai:ri.conicet.gov.ar:11336/6063instacron: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:34982025-09-29 09:34:47.145CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
title Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
spellingShingle Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
Martins, Guilherme M.
3h-Benzo[E]Indoles
Heterocycles
Iodocyclization
Phenylacetylenes
title_short Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
title_full Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
title_fullStr Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
title_full_unstemmed Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
title_sort Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
dc.creator.none.fl_str_mv Martins, Guilherme M.
Zeni, Gilson
Back, David F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author Martins, Guilherme M.
author_facet Martins, Guilherme M.
Zeni, Gilson
Back, David F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author_role author
author2 Zeni, Gilson
Back, David F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author2_role author
author
author
author
dc.subject.none.fl_str_mv 3h-Benzo[E]Indoles
Heterocycles
Iodocyclization
Phenylacetylenes
topic 3h-Benzo[E]Indoles
Heterocycles
Iodocyclization
Phenylacetylenes
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.
Fil: Martins, Guilherme M.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Zeni, Gilson. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Back, David F.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Qu ímica; Brasil
description A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.
publishDate 2015
dc.date.none.fl_str_mv 2015-10-12
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/11336/6063
Martins, Guilherme M.; Zeni, Gilson; Back, David F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles; Wiley; Advanced Synthesis & Catalysis (print); 357; 14-15; 12-10-2015; 3255-3261
1615-4150
url http://hdl.handle.net/11336/6063
identifier_str_mv Martins, Guilherme M.; Zeni, Gilson; Back, David F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles; Wiley; Advanced Synthesis & Catalysis (print); 357; 14-15; 12-10-2015; 3255-3261
1615-4150
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500275/abstract
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201500275
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
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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 13.070432

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