Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline

New green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time....

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Fecha de publicación:
2013
Institución:
Ministerio de Ciencia Tecnología e Innovación
Repositorio:
Repositorio Institucional de Minciencias
Idioma:
eng
OAI Identifier:
oai:repositorio.minciencias.gov.co:20.500.14143/34157
Acceso en línea:
http://repositorio.colciencias.gov.co/handle/11146/34157
Palabra clave:
Aceites vegetales
Biología vegetal
Aceites esenciales
Botánica
Bioquímica vegetal
Tecnología química
Química agrícola
Catalizadores
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http://purl.org/coar/access_right/c_f1cf
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network_name_str Repositorio Institucional de Minciencias
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spelling Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinolineAceites vegetalesBiología vegetalAceites esencialesBotánicaBioquímica vegetalTecnología químicaQuímica agrícolaCatalizadoresNew green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time. The influence of the SDS micelles and their different concentrations (5.0, 8.2 and 12.0 mM) on reactivity of the imino Diels–Alder reaction was studied. It was found that the best THQ yields (70–99%) are achieved above the critical micellar concentration (12 mM) using pH 1.0–2.5. This procedure resulted in a general and clean environmentally benign protocol to obtain the privileged diastereospecific cis 2,4-disubstituted THQ molecules of highest biological interest.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 colombianano2019-03-31T22:50:01Z2019-03-31T22:50:01Z2013info:eu-repo/date/embargoEnd/2024-01-31Artículo científicoinfo:eu-repo/semantics/articlehttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1pdf9 páginasapplication/pdfhttp://repositorio.colciencias.gov.co/handle/11146/34157Contiene 45 referencias bibliográficas. Véase documento adjunto10.1039/c3ob40171eOrganic & Biomolecular Chemistry 2013, 11, 3655-3663engPrograma: 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>Colombiahttp://purl.org/coar/access_right/c_f1cfMerchan Arenas, Diego RolandoMartínez Bonilla, Carlos A.Kouznetsov, Vladimir V.oai:repositorio.minciencias.gov.co:20.500.14143/341572023-11-29T17:32:15Z
dc.title.none.fl_str_mv Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
title Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
spellingShingle Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
Aceites vegetales
Biología vegetal
Aceites esenciales
Botánica
Bioquímica vegetal
Tecnología química
Química agrícola
Catalizadores
title_short Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
title_full Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
title_fullStr Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
title_full_unstemmed Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
title_sort Aqueous SDS micelle-promoted acid-catalyzed domino ABB’ imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyltetrahydroquinoline
dc.subject.none.fl_str_mv Aceites vegetales
Biología vegetal
Aceites esenciales
Botánica
Bioquímica vegetal
Tecnología química
Química agrícola
Catalizadores
topic Aceites vegetales
Biología vegetal
Aceites esenciales
Botánica
Bioquímica vegetal
Tecnología química
Química agrícola
Catalizadores
description New green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB’ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time. The influence of the SDS micelles and their different concentrations (5.0, 8.2 and 12.0 mM) on reactivity of the imino Diels–Alder reaction was studied. It was found that the best THQ yields (70–99%) are achieved above the critical micellar concentration (12 mM) using pH 1.0–2.5. This procedure resulted in a general and clean environmentally benign protocol to obtain the privileged diastereospecific cis 2,4-disubstituted THQ molecules of highest biological interest.
publishDate 2013
dc.date.none.fl_str_mv 2013
2019-03-31T22:50:01Z
2019-03-31T22:50:01Z
info:eu-repo/date/embargoEnd/2024-01-31
dc.type.none.fl_str_mv Artículo científico
info:eu-repo/semantics/article
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.identifier.none.fl_str_mv http://repositorio.colciencias.gov.co/handle/11146/34157
Contiene 45 referencias bibliográficas. Véase documento adjunto
10.1039/c3ob40171e
url http://repositorio.colciencias.gov.co/handle/11146/34157
identifier_str_mv Contiene 45 referencias bibliográficas. Véase documento adjunto
10.1039/c3ob40171e
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.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>
dc.rights.coar.fl_str_mv http://purl.org/coar/access_right/c_f1cf
rights_invalid_str_mv http://purl.org/coar/access_right/c_f1cf
dc.format.none.fl_str_mv pdf
9 páginas
application/pdf
dc.coverage.none.fl_str_mv Colombia
dc.source.none.fl_str_mv Organic & Biomolecular Chemistry 2013, 11, 3655-3663
institution Ministerio de Ciencia Tecnología e Innovación
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1860676500750073856

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