Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives
- Autores
- Muscia, Gisela Celeste; de María, Leonardo Oscar; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth
- Año de publicación
- 2016
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method.
Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: de María, Leonardo Oscar. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Buldain, Graciela Yolanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Asís, Silvia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina - Materia
-
Sonication
Beta-Carbolines
Synthesis
Pictet-Spengler - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/39633
Ver los metadatos del registro completo
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Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline DerivativesMuscia, Gisela Celestede María, Leonardo OscarBuldain, Graciela YolandaAsís, Silvia ElizabethSonicationBeta-CarbolinesSynthesisPictet-Spenglerhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method.Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: de María, Leonardo Oscar. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Buldain, Graciela Yolanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Asís, Silvia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaWiley Blackwell Publishing, Inc2016-03info: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/11336/39633Muscia, Gisela Celeste; de María, Leonardo Oscar; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives; Wiley Blackwell Publishing, Inc; Journal of Heterocyclic Chemistry; 53; 2; 3-2016; 647-6500022-152XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jhet.2318/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1002/jhet.2318info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:51:10Zoai:ri.conicet.gov.ar:11336/39633instacron: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 09:51:10.766CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
title |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
spellingShingle |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives Muscia, Gisela Celeste Sonication Beta-Carbolines Synthesis Pictet-Spengler |
title_short |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
title_full |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
title_fullStr |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
title_full_unstemmed |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
title_sort |
Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives |
dc.creator.none.fl_str_mv |
Muscia, Gisela Celeste de María, Leonardo Oscar Buldain, Graciela Yolanda Asís, Silvia Elizabeth |
author |
Muscia, Gisela Celeste |
author_facet |
Muscia, Gisela Celeste de María, Leonardo Oscar Buldain, Graciela Yolanda Asís, Silvia Elizabeth |
author_role |
author |
author2 |
de María, Leonardo Oscar Buldain, Graciela Yolanda Asís, Silvia Elizabeth |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
Sonication Beta-Carbolines Synthesis Pictet-Spengler |
topic |
Sonication Beta-Carbolines Synthesis Pictet-Spengler |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method. Fil: Muscia, Gisela Celeste. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina Fil: de María, Leonardo Oscar. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina Fil: Buldain, Graciela Yolanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina Fil: Asís, Silvia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina |
description |
The synthesis of twelve tetrahydro-β-carboline derivatives 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l prepared via the Pictet-Spengler reaction is described. The reaction of tryptamine and a variety of arylaldehydes were carried out under ultrasonic irradiation and trifluoracetic acid catalysis at room temperature. These tetrahydro-β-carbolines have been synthesized in higher yields and shorter reaction times compared to the conventional method. Moreover, the reaction proceeded successfully even employing arylaldehydes with electron-donating or electron-attracting substituents which did not react under conventional method. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-03 |
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/11336/39633 Muscia, Gisela Celeste; de María, Leonardo Oscar; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives; Wiley Blackwell Publishing, Inc; Journal of Heterocyclic Chemistry; 53; 2; 3-2016; 647-650 0022-152X CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/39633 |
identifier_str_mv |
Muscia, Gisela Celeste; de María, Leonardo Oscar; Buldain, Graciela Yolanda; Asís, Silvia Elizabeth; Ultrasound Assisted Pictet-Spengler Synthesis of Tetrahydro-β-Carboline Derivatives; Wiley Blackwell Publishing, Inc; Journal of Heterocyclic Chemistry; 53; 2; 3-2016; 647-650 0022-152X CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/jhet.2318/abstract info:eu-repo/semantics/altIdentifier/doi/10.1002/jhet.2318 |
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 |
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 |
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1842269077843738624 |
score |
13.13397 |