Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles

2-Substituted benzothiazoles were efficiently synthesized by radical cyclization of thioformanilides induced by chloranil under irradiation in 1,2-dichloroethane and toluene at 80 °C. Hydrogen atom abstraction from thiobenzamide by triplet chloranil was the key step of the mechanism, as confirmed by...

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Autores: Rey, Valentina, Soria Castro, Silvia Mercedes, Argüello, Juan Elias, Peñeñory, Alicia Beatriz
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2009
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/72538
Acesso em linha:http://hdl.handle.net/11336/72538
Access Level:acceso abierto
Palavra-chave:Photochemistry
Benzothiazoles
Chloranil
Laser Flash Photolysis
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazolesRey, ValentinaSoria Castro, Silvia MercedesArgüello, Juan EliasPeñeñory, Alicia BeatrizPhotochemistryBenzothiazolesChloranilLaser Flash Photolysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/12-Substituted benzothiazoles were efficiently synthesized by radical cyclization of thioformanilides induced by chloranil under irradiation in 1,2-dichloroethane and toluene at 80 °C. Hydrogen atom abstraction from thiobenzamide by triplet chloranil was the key step of the mechanism, as confirmed by LFP experiments. The methodology developed is simple and afforded the easily isolated products from moderate to good yield. © 2009 Elsevier Ltd. All rights reserved.Fil: Rey, Valentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Soria Castro, Silvia Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Peñeñory, Alicia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaPergamon-Elsevier Science Ltd2009-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/72538Rey, Valentina; Soria Castro, Silvia Mercedes; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 50; 33; 8-2009; 4720-47230040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/https://www.sciencedirect.com/science/article/pii/S0040403909011733info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2009.06.020info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:03:28Zoai:ri.conicet.gov.ar:11336/72538instacron: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:34982024-05-08 14:03:28.857CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
title Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
spellingShingle Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
Rey, Valentina
Photochemistry
Benzothiazoles
Chloranil
Laser Flash Photolysis
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
title_full Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
title_fullStr Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
title_full_unstemmed Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
title_sort Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles
dc.creator.none.fl_str_mv Rey, Valentina
Soria Castro, Silvia Mercedes
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author Rey, Valentina
author_facet Rey, Valentina
Soria Castro, Silvia Mercedes
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author_role author
author2 Soria Castro, Silvia Mercedes
Argüello, Juan Elias
Peñeñory, Alicia Beatriz
author2_role author
author
author
dc.subject.none.fl_str_mv Photochemistry
Benzothiazoles
Chloranil
Laser Flash Photolysis
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Photochemistry
Benzothiazoles
Chloranil
Laser Flash Photolysis
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description 2-Substituted benzothiazoles were efficiently synthesized by radical cyclization of thioformanilides induced by chloranil under irradiation in 1,2-dichloroethane and toluene at 80 °C. Hydrogen atom abstraction from thiobenzamide by triplet chloranil was the key step of the mechanism, as confirmed by LFP experiments. The methodology developed is simple and afforded the easily isolated products from moderate to good yield. © 2009 Elsevier Ltd. All rights reserved.
publishDate 2009
dc.date.none.fl_str_mv 2009-08
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/11336/72538
Rey, Valentina; Soria Castro, Silvia Mercedes; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 50; 33; 8-2009; 4720-4723
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/72538
identifier_str_mv Rey, Valentina; Soria Castro, Silvia Mercedes; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Photochemical cyclization of thioformanilides by chloranil: An approach to 2-substituted benzothiazoles; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 50; 33; 8-2009; 4720-4723
0040-4039
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/https://www.sciencedirect.com/science/article/pii/S0040403909011733
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2009.06.020
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
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,811543

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