Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions

Autores
Padilha, Gustavo; Iglesias, Bernardo A.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new approach toward chromeno[4,3-b]pyrrol-4(1H)-ones, by annulation of 4-phenylaminocoumarins with β-nitroalkenes, is reported and its conditions were optimized. The transformations under the fine-tuned conditions took place under promotion by TsOH.H2O, in the absence of solvent. The scope and limitations of the process were explored, by systematic modification of two diversification points. A reaction mechanism, triggered by a Michael addition of the nitrogen moiety of the 4-phenylaminocoumarins to the β-nitroalkene, was also proposed. Further functionalization of a selected tricycle was performed; the photophysical (UV and fluorescence spectra; 1O2 generation) and electrochemical (cyclic voltammetry) properties of some heterocycles were studied.
Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; Brasil
Fil: Iglesias, Bernardo A.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
Materia
Chromeno[4,3-B]Pyrrol-4(1h)-Ones
Condensed Heterocycles
Cyclization
Tsoh-Promoted Solvent-Free Reaction
Β-Nitrostyrenes
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:11336/63869
Acceder
id CONICETDig_12f5ae17cb0e9462159069fa9997171e
oai_identifier_str oai:ri.conicet.gov.ar:11336/63869
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free ConditionsPadilha, GustavoIglesias, Bernardo A.Back, Davi F.Kaufman, Teodoro SaulSilveira, Claudio C.Chromeno[4,3-B]Pyrrol-4(1h)-OnesCondensed HeterocyclesCyclizationTsoh-Promoted Solvent-Free ReactionΒ-Nitrostyreneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new approach toward chromeno[4,3-b]pyrrol-4(1H)-ones, by annulation of 4-phenylaminocoumarins with β-nitroalkenes, is reported and its conditions were optimized. The transformations under the fine-tuned conditions took place under promotion by TsOH.H2O, in the absence of solvent. The scope and limitations of the process were explored, by systematic modification of two diversification points. A reaction mechanism, triggered by a Michael addition of the nitrogen moiety of the 4-phenylaminocoumarins to the β-nitroalkene, was also proposed. Further functionalization of a selected tricycle was performed; the photophysical (UV and fluorescence spectra; 1O2 generation) and electrochemical (cyclic voltammetry) properties of some heterocycles were studied.Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; BrasilFil: Iglesias, Bernardo A.. Universidade Federal de Santa Maria; BrasilFil: Back, Davi F.. Universidade Federal de Santa Maria; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio C.. Universidade Federal de Santa Maria; BrasilWiley Blackwell Publishing, Inc2017-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/63869Padilha, Gustavo; Iglesias, Bernardo A.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions; Wiley Blackwell Publishing, Inc; ChemistrySelect; 2; 3; 1-2017; 1297-13042365-6549CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/slct.201700114info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/slct.201700114info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:35:40Zoai:ri.conicet.gov.ar:11336/63869instacron: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:34982025-10-15 15:35:40.744CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
title Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
spellingShingle Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
Padilha, Gustavo
Chromeno[4,3-B]Pyrrol-4(1h)-Ones
Condensed Heterocycles
Cyclization
Tsoh-Promoted Solvent-Free Reaction
Β-Nitrostyrenes
title_short Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
title_full Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
title_fullStr Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
title_full_unstemmed Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
title_sort Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions
dc.creator.none.fl_str_mv Padilha, Gustavo
Iglesias, Bernardo A.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author Padilha, Gustavo
author_facet Padilha, Gustavo
Iglesias, Bernardo A.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author_role author
author2 Iglesias, Bernardo A.
Back, Davi F.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Chromeno[4,3-B]Pyrrol-4(1h)-Ones
Condensed Heterocycles
Cyclization
Tsoh-Promoted Solvent-Free Reaction
Β-Nitrostyrenes
topic Chromeno[4,3-B]Pyrrol-4(1h)-Ones
Condensed Heterocycles
Cyclization
Tsoh-Promoted Solvent-Free Reaction
Β-Nitrostyrenes
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 new approach toward chromeno[4,3-b]pyrrol-4(1H)-ones, by annulation of 4-phenylaminocoumarins with β-nitroalkenes, is reported and its conditions were optimized. The transformations under the fine-tuned conditions took place under promotion by TsOH.H2O, in the absence of solvent. The scope and limitations of the process were explored, by systematic modification of two diversification points. A reaction mechanism, triggered by a Michael addition of the nitrogen moiety of the 4-phenylaminocoumarins to the β-nitroalkene, was also proposed. Further functionalization of a selected tricycle was performed; the photophysical (UV and fluorescence spectra; 1O2 generation) and electrochemical (cyclic voltammetry) properties of some heterocycles were studied.
Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; Brasil
Fil: Iglesias, Bernardo A.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
description A new approach toward chromeno[4,3-b]pyrrol-4(1H)-ones, by annulation of 4-phenylaminocoumarins with β-nitroalkenes, is reported and its conditions were optimized. The transformations under the fine-tuned conditions took place under promotion by TsOH.H2O, in the absence of solvent. The scope and limitations of the process were explored, by systematic modification of two diversification points. A reaction mechanism, triggered by a Michael addition of the nitrogen moiety of the 4-phenylaminocoumarins to the β-nitroalkene, was also proposed. Further functionalization of a selected tricycle was performed; the photophysical (UV and fluorescence spectra; 1O2 generation) and electrochemical (cyclic voltammetry) properties of some heterocycles were studied.
publishDate 2017
dc.date.none.fl_str_mv 2017-01
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/11336/63869
Padilha, Gustavo; Iglesias, Bernardo A.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions; Wiley Blackwell Publishing, Inc; ChemistrySelect; 2; 3; 1-2017; 1297-1304
2365-6549
CONICET Digital
CONICET
url http://hdl.handle.net/11336/63869
identifier_str_mv Padilha, Gustavo; Iglesias, Bernardo A.; Back, Davi F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones, from β-Nitroalkenes and 4-Phenylaminocoumarins, under Solvent–free Conditions; Wiley Blackwell Publishing, Inc; ChemistrySelect; 2; 3; 1-2017; 1297-1304
2365-6549
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/slct.201700114
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/slct.201700114
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 Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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_ 1846083482236747776
score 13.221938

Publicaciones similares