Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives

Autores
Martín-Acosta, Pedro; Feresin, Gabriela Egly; Tapia, Alejandro; Estevez Braun, Ana
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels−Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
Fil: Martín-Acosta, Pedro. Universidad de La Laguna; España
Fil: Feresin, Gabriela Egly. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Juan; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan; Argentina
Fil: Estevez Braun, Ana. Universidad de La Laguna; España
Materia
Microwave
Embelin Derivatives
Synthesis
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:11336/47113
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin DerivativesMartín-Acosta, PedroFeresin, Gabriela EglyTapia, AlejandroEstevez Braun, AnaMicrowaveEmbelin DerivativesSynthesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels−Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.Fil: Martín-Acosta, Pedro. Universidad de La Laguna; EspañaFil: Feresin, Gabriela Egly. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Juan; ArgentinaFil: Tapia, Alejandro. Universidad Nacional de San Juan; ArgentinaFil: Estevez Braun, Ana. Universidad de La Laguna; EspañaAmerican Chemical Society2016-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/47113Martín-Acosta, Pedro; Feresin, Gabriela Egly; Tapia, Alejandro; Estevez Braun, Ana; Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives; American Chemical Society; Journal of Organic Chemistry; 81; 20; 10-2016; 9738-97560022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.6b01818info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b01818info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:50:34Zoai:ri.conicet.gov.ar:11336/47113instacron: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:34982025-09-03 09:50:34.49CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
title Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
spellingShingle Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
Martín-Acosta, Pedro
Microwave
Embelin Derivatives
Synthesis
title_short Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
title_full Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
title_fullStr Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
title_full_unstemmed Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
title_sort Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives
dc.creator.none.fl_str_mv Martín-Acosta, Pedro
Feresin, Gabriela Egly
Tapia, Alejandro
Estevez Braun, Ana
author Martín-Acosta, Pedro
author_facet Martín-Acosta, Pedro
Feresin, Gabriela Egly
Tapia, Alejandro
Estevez Braun, Ana
author_role author
author2 Feresin, Gabriela Egly
Tapia, Alejandro
Estevez Braun, Ana
author2_role author
author
author
dc.subject.none.fl_str_mv Microwave
Embelin Derivatives
Synthesis
topic Microwave
Embelin Derivatives
Synthesis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels−Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
Fil: Martín-Acosta, Pedro. Universidad de La Laguna; España
Fil: Feresin, Gabriela Egly. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de San Juan; Argentina
Fil: Tapia, Alejandro. Universidad Nacional de San Juan; Argentina
Fil: Estevez Braun, Ana. Universidad de La Laguna; España
description highly efficient and regioselective approach to new polycyclic embelin derivatives through a domino Knoevenagel condensation/intramolecular hetero Diels−Alder reaction using O-(arylpropynyloxy)-salicylaldehydes in the presence of ethylenediamine diacetate (EDDA) is reported. This organocatalyzed protocol is compatible toward a wide range of aryl-substituted alkynyl ethers with electron-donating and electron-withdrawing groups. When other active methylene compounds were subjected to this domino reaction the corresponding adducts were obtained in high yield.
publishDate 2016
dc.date.none.fl_str_mv 2016-10
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/11336/47113
Martín-Acosta, Pedro; Feresin, Gabriela Egly; Tapia, Alejandro; Estevez Braun, Ana; Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives; American Chemical Society; Journal of Organic Chemistry; 81; 20; 10-2016; 9738-9756
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47113
identifier_str_mv Martín-Acosta, Pedro; Feresin, Gabriela Egly; Tapia, Alejandro; Estevez Braun, Ana; Microwave-Assisted Organocatalytic Intramolecular Knoevenagel/Hetero Diels–Alder Reaction with O -(Arylpropynyloxy)-Salicylaldehydes: Synthesis of Polycyclic Embelin Derivatives; American Chemical Society; Journal of Organic Chemistry; 81; 20; 10-2016; 9738-9756
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.6b01818
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.6b01818
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.13397

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