Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin

Autores
Scoccia, Jimena; Castro, Maria Julia; Faraoni, María Belén; Bouzat, Cecilia Beatriz; Martín García, Victor Sotero; Gerbino, Darío César
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.
Fil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Castro, Maria Julia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Bouzat, Cecilia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; Argentina
Fil: Martín García, Victor Sotero. Universidad de La Laguna; España
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Materia
Dibenzo[B,E]Oxepin-11(6h)-Ones
Intramolecular Acylation
Anthelmintic Activity
Synthetic Methodology
Doxepin
Anthelmintic Activity
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:11336/41015
Acceder
id CONICETDig_481cea68f59590fca12f67dd1450196f
oai_identifier_str oai:ri.conicet.gov.ar:11336/41015
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepinScoccia, JimenaCastro, Maria JuliaFaraoni, María BelénBouzat, Cecilia BeatrizMartín García, Victor SoteroGerbino, Darío CésarDibenzo[B,E]Oxepin-11(6h)-OnesIntramolecular AcylationAnthelmintic ActivitySynthetic MethodologyDoxepinAnthelmintic Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.Fil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Castro, Maria Julia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Bouzat, Cecilia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; ArgentinaFil: Martín García, Victor Sotero. Universidad de La Laguna; EspañaFil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaPergamon-Elsevier Science Ltd2017-05-18info: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/11336/41015Scoccia, Jimena; Castro, Maria Julia; Faraoni, María Belén; Bouzat, Cecilia Beatriz; Martín García, Victor Sotero; et al.; Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin; Pergamon-Elsevier Science Ltd; Tetrahedron; 73; 20; 18-5-2017; 2913-29220040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402017303423info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2017.03.085info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:25:05Zoai:ri.conicet.gov.ar:11336/41015instacron: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 14:25:05.37CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
title Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
spellingShingle Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
Scoccia, Jimena
Dibenzo[B,E]Oxepin-11(6h)-Ones
Intramolecular Acylation
Anthelmintic Activity
Synthetic Methodology
Doxepin
Anthelmintic Activity
title_short Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
title_full Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
title_fullStr Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
title_full_unstemmed Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
title_sort Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
dc.creator.none.fl_str_mv Scoccia, Jimena
Castro, Maria Julia
Faraoni, María Belén
Bouzat, Cecilia Beatriz
Martín García, Victor Sotero
Gerbino, Darío César
author Scoccia, Jimena
author_facet Scoccia, Jimena
Castro, Maria Julia
Faraoni, María Belén
Bouzat, Cecilia Beatriz
Martín García, Victor Sotero
Gerbino, Darío César
author_role author
author2 Castro, Maria Julia
Faraoni, María Belén
Bouzat, Cecilia Beatriz
Martín García, Victor Sotero
Gerbino, Darío César
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Dibenzo[B,E]Oxepin-11(6h)-Ones
Intramolecular Acylation
Anthelmintic Activity
Synthetic Methodology
Doxepin
Anthelmintic Activity
topic Dibenzo[B,E]Oxepin-11(6h)-Ones
Intramolecular Acylation
Anthelmintic Activity
Synthetic Methodology
Doxepin
Anthelmintic Activity
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 novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.
Fil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Castro, Maria Julia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Bouzat, Cecilia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Investigaciones Bioquímicas de Bahía Blanca. Universidad Nacional del Sur. Instituto de Investigaciones Bioquímicas de Bahía Blanca; Argentina
Fil: Martín García, Victor Sotero. Universidad de La Laguna; España
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
description A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.
publishDate 2017
dc.date.none.fl_str_mv 2017-05-18
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/11336/41015
Scoccia, Jimena; Castro, Maria Julia; Faraoni, María Belén; Bouzat, Cecilia Beatriz; Martín García, Victor Sotero; et al.; Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin; Pergamon-Elsevier Science Ltd; Tetrahedron; 73; 20; 18-5-2017; 2913-2922
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/41015
identifier_str_mv Scoccia, Jimena; Castro, Maria Julia; Faraoni, María Belén; Bouzat, Cecilia Beatriz; Martín García, Victor Sotero; et al.; Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin; Pergamon-Elsevier Science Ltd; Tetrahedron; 73; 20; 18-5-2017; 2913-2922
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/url/https://www.sciencedirect.com/science/article/pii/S0040402017303423
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2017.03.085
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.22299

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