Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest

Diverse natural product-like N-benzyl cinnamamides were prepared by condensation of trans-cinnamic acid with substituted benzylamines in the presence of boric acid as catalyst. The further evaluation of this amides as a substrates of the bromo-arylation reaction, in the presence of N-bromosuccinimid...

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Fecha de publicación:
2013
Institución:
Ministerio de Ciencia, Tecnología e Innovación
Repositorio:
Repositorio Minciencias
Idioma:
eng
OAI Identifier:
oai:repositorio.minciencias.gov.co:20.500.14143/34189
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http://repositorio.colciencias.gov.co/handle/11146/34189
Palabra clave:
Biología vegetal
Productos farmacéuticos
Plantas medicinales
N-Aryl 2,3-dibromopropanamides
N-Benzyl cinnamamides
Boric acid
N-(2-Bromobenzyl) cinnamamides
Tetrahydro-2- benzazepin-3-ones
Yb(OTf)3-Catalyzed bromination reactions
Tecnología química
Bioquímica vegetal
Biomasa
Aceites esenciales
Rights
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http://purl.org/coar/access_right/c_f1cf
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spelling Colombia2019-04-01T04:11:28Z2019-04-01T04:11:28Z2013info:eu-repo/date/embargoEnd/2024-01-311875-5348http://repositorio.colciencias.gov.co/handle/11146/34189Contiene 27 referencias bibliográficas. Véase documento adjuntoDiverse natural product-like N-benzyl cinnamamides were prepared by condensation of trans-cinnamic acid with substituted benzylamines in the presence of boric acid as catalyst. The further evaluation of this amides as a substrates of the bromo-arylation reaction, in the presence of N-bromosuccinimide (NBS) as the halogen source and under the catalysis of Yb(OTf)3, generate a different types of N-substituted amides: N-aryl 2,3-dibromopropanamides, N-(2-bromobenzyl) cinnamamides and tetrahydro-2-benzazepin-3-one as a new molecules. Here we discuss the formation of these main products on the basis of the electronic nature of the substituents present in the N-benzyl aromatic ring of the prepared cinnamamides.Departamento Administrativo de Ciencia, Tecnología e Innovación [CO] Colciencias5507-543-31904Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombiananopdf10 páginasengPrograma: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombiana. La publicación completa está disponible en : <a href="http://repositorio.colciencias.gov.co/handle/11146/34163" target="blank">http://repositorio.colciencias.gov.co/handle/11146/34163</a>Current Organic Chemistry, 2013, 17, 1545-1554Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological InterestArtículo científicoinfo:eu-repo/semantics/articlehttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1Administradores de ciencia y tecnologíaInvestigadoresBiología vegetalProductos farmacéuticosPlantas medicinalesN-Aryl 2,3-dibromopropanamidesN-Benzyl cinnamamidesBoric acidN-(2-Bromobenzyl) cinnamamidesTetrahydro-2- benzazepin-3-onesYb(OTf)3-Catalyzed bromination reactionsTecnología químicaBioquímica vegetalBiomasaAceites esencialeshttp://purl.org/coar/access_right/c_f1cfPuerto Galvis, Carlos EduardoHernandez Barajas, José G.Kouznetsov, Vladimir V.Bio-Red-CO-CENIVAMUniversidad Industrial de Santander, UISkouznet@uis.edu.co2018-01Programas de CT+I Ejecutados por Redes de ConocimientoComunidad científica colombiana0572-2012Artículos de investigaciónPublicationORIGINALART_YB~1.PDFART_YB~1.PDFArtículo Current Organic Chemistryapplication/pdf437548https://repositorio.minciencias.gov.co/bitstreams/33f73951-2982-4f68-97f5-e3d594929009/download3ffecb217ccce3154e8693a1f8dddb7bMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://repositorio.minciencias.gov.co/bitstreams/85382170-b48c-4da2-ae02-39bc09b8bb46/download8a4605be74aa9ea9d79846c1fba20a33MD52TEXTART_YB~1.PDF.txtART_YB~1.PDF.txtExtracted texttext/plain54451https://repositorio.minciencias.gov.co/bitstreams/20a9d62d-c270-485d-8fd3-2a08592fd362/download1fd3e5f313cfc6936d46a670be359179MD55THUMBNAILART_YB~1.PDF.jpgART_YB~1.PDF.jpgGenerated Thumbnailimage/jpeg14136https://repositorio.minciencias.gov.co/bitstreams/c09dfa50-cbac-4121-86e7-a9b4d701d7b2/download2aab59ba89f28ee1eba93bff99cb1251MD5620.500.14143/34189oai:repositorio.minciencias.gov.co:20.500.14143/341892023-11-29 17:31:15.434restrictedhttps://repositorio.minciencias.gov.coRepositorio Institucional de Mincienciascendoc@minciencias.gov.co
dc.title.es_CO.fl_str_mv Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
title Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
spellingShingle Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
Biología vegetal
Productos farmacéuticos
Plantas medicinales
N-Aryl 2,3-dibromopropanamides
N-Benzyl cinnamamides
Boric acid
N-(2-Bromobenzyl) cinnamamides
Tetrahydro-2- benzazepin-3-ones
Yb(OTf)3-Catalyzed bromination reactions
Tecnología química
Bioquímica vegetal
Biomasa
Aceites esenciales
title_short Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
title_full Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
title_fullStr Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
title_full_unstemmed Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
title_sort Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest
dc.subject.lemb.es_CO.fl_str_mv Biología vegetal
Productos farmacéuticos
Plantas medicinales
topic Biología vegetal
Productos farmacéuticos
Plantas medicinales
N-Aryl 2,3-dibromopropanamides
N-Benzyl cinnamamides
Boric acid
N-(2-Bromobenzyl) cinnamamides
Tetrahydro-2- benzazepin-3-ones
Yb(OTf)3-Catalyzed bromination reactions
Tecnología química
Bioquímica vegetal
Biomasa
Aceites esenciales
dc.subject.keyword.none.fl_str_mv N-Aryl 2,3-dibromopropanamides
N-Benzyl cinnamamides
Boric acid
N-(2-Bromobenzyl) cinnamamides
Tetrahydro-2- benzazepin-3-ones
Yb(OTf)3-Catalyzed bromination reactions
dc.subject.spines.es_CO.fl_str_mv Tecnología química
Bioquímica vegetal
Biomasa
Aceites esenciales
description Diverse natural product-like N-benzyl cinnamamides were prepared by condensation of trans-cinnamic acid with substituted benzylamines in the presence of boric acid as catalyst. The further evaluation of this amides as a substrates of the bromo-arylation reaction, in the presence of N-bromosuccinimide (NBS) as the halogen source and under the catalysis of Yb(OTf)3, generate a different types of N-substituted amides: N-aryl 2,3-dibromopropanamides, N-(2-bromobenzyl) cinnamamides and tetrahydro-2-benzazepin-3-one as a new molecules. Here we discuss the formation of these main products on the basis of the electronic nature of the substituents present in the N-benzyl aromatic ring of the prepared cinnamamides.
publishDate 2013
dc.date.issued.none.fl_str_mv 2013
dc.date.accessioned.none.fl_str_mv 2019-04-01T04:11:28Z
dc.date.available.none.fl_str_mv 2019-04-01T04:11:28Z
dc.date.embargoEnd.es_CO.fl_str_mv info:eu-repo/date/embargoEnd/2024-01-31
dc.type.es_CO.fl_str_mv Artículo científico
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.driver.es_CO.fl_str_mv info:eu-repo/semantics/article
dc.identifier.issn.none.fl_str_mv 1875-5348
dc.identifier.uri.none.fl_str_mv http://repositorio.colciencias.gov.co/handle/11146/34189
dc.identifier.bibliographicCitation.es_CO.fl_str_mv Contiene 27 referencias bibliográficas. Véase documento adjunto
identifier_str_mv 1875-5348
Contiene 27 referencias bibliográficas. Véase documento adjunto
url http://repositorio.colciencias.gov.co/handle/11146/34189
dc.language.iso.es_CO.fl_str_mv eng
language eng
dc.relation.ispartof.es_CO.fl_str_mv Programa: Bioprospección y desarrollo de ingredientes naturales para las industrias cosmética, farmacéutica y de productos de aseo con base en la biodiversidad colombiana. La publicación completa está disponible en : <a href="http://repositorio.colciencias.gov.co/handle/11146/34163" target="blank">http://repositorio.colciencias.gov.co/handle/11146/34163</a>
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dc.format.extent.es_CO.fl_str_mv 10 páginas
dc.coverage.spatial.es_CO.fl_str_mv Colombia
dc.source.es_CO.fl_str_mv Current Organic Chemistry, 2013, 17, 1545-1554
institution Ministerio de Ciencia, Tecnología e Innovación
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