Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization

Detalhes bibliográficos
Autor(a) principal: Ferreira, Isabel C. F. R.
Data de Publicação: 2002
Outros Autores: Queiroz, Maria João R. P., Kirsch, G.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/2255
Resumo: Palladium or copper catalyzed aminations or amidations were performed to obtain diarylamines and diarylacetamides precursors of thienocarbazoles. The fact that an ortho-bromodiarylamine didn’t cyclize to the corresponding thienocarbazole under conditions known for carbazoles from ortho-halodiphenylamines, conducted us to a highgly efficient method of palladium-catalyzed intramolecular cyclisation with N-deprotection of ortho-halodiarylacetamides to thienocarbazoles. Other method of intramolecular cyclization of diarylamines based on the reoxidation of the Pd(0) formed by Cu(OAc)2 , avoiding the use of stoichiometric amounts of Pd(OAc)2, gave thienocarbazoles in a moderate yield, including a ring A methoxylated compound. An attempt to combine palladium and copper catalyses in a “one pot” reaction of amination and intramolecular cyclization gave as major product a N-benzo[b]thiophene substituted carbazole and the required thienocarbazole in low yield.
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spelling Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclizationC-N couplingCopperPalladiumCyclization-deprotectionThienocarbazolesScience & TechnologyPalladium or copper catalyzed aminations or amidations were performed to obtain diarylamines and diarylacetamides precursors of thienocarbazoles. The fact that an ortho-bromodiarylamine didn’t cyclize to the corresponding thienocarbazole under conditions known for carbazoles from ortho-halodiphenylamines, conducted us to a highgly efficient method of palladium-catalyzed intramolecular cyclisation with N-deprotection of ortho-halodiarylacetamides to thienocarbazoles. Other method of intramolecular cyclization of diarylamines based on the reoxidation of the Pd(0) formed by Cu(OAc)2 , avoiding the use of stoichiometric amounts of Pd(OAc)2, gave thienocarbazoles in a moderate yield, including a ring A methoxylated compound. An attempt to combine palladium and copper catalyses in a “one pot” reaction of amination and intramolecular cyclization gave as major product a N-benzo[b]thiophene substituted carbazole and the required thienocarbazole in low yield.Thanks are due to Foundation for the Science and Technology-IBQF-Univ.Minho (Portugal) for financial support, to the Research Incitment Programme of the Calouste Gulbenkian Foundation (Portugal) and to Escola Superior Agrária - Instituto Politécnico de Bragança for supporting in part Isabel C. F.R. Ferreira PhD.ElsevierUniversidade do MinhoFerreira, Isabel C. F. R.Queiroz, Maria João R. P.Kirsch, G.20022002-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/2255engFerreira, I. C. F. R., Queiroz, M.-J. R. P., & Kirsch, G. (2002, September). Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization. Tetrahedron. Elsevier BV. http://doi.org/10.1016/s0040-4020(02)00904-30040-402010.1016/S0040-4020(02)00904-3info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:13:19Zoai:repositorium.sdum.uminho.pt:1822/2255Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:05:22.898001Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
title Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
spellingShingle Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
Ferreira, Isabel C. F. R.
C-N coupling
Copper
Palladium
Cyclization-deprotection
Thienocarbazoles
Science & Technology
title_short Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
title_full Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
title_fullStr Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
title_full_unstemmed Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
title_sort Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
author Ferreira, Isabel C. F. R.
author_facet Ferreira, Isabel C. F. R.
Queiroz, Maria João R. P.
Kirsch, G.
author_role author
author2 Queiroz, Maria João R. P.
Kirsch, G.
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Ferreira, Isabel C. F. R.
Queiroz, Maria João R. P.
Kirsch, G.
dc.subject.por.fl_str_mv C-N coupling
Copper
Palladium
Cyclization-deprotection
Thienocarbazoles
Science & Technology
topic C-N coupling
Copper
Palladium
Cyclization-deprotection
Thienocarbazoles
Science & Technology
description Palladium or copper catalyzed aminations or amidations were performed to obtain diarylamines and diarylacetamides precursors of thienocarbazoles. The fact that an ortho-bromodiarylamine didn’t cyclize to the corresponding thienocarbazole under conditions known for carbazoles from ortho-halodiphenylamines, conducted us to a highgly efficient method of palladium-catalyzed intramolecular cyclisation with N-deprotection of ortho-halodiarylacetamides to thienocarbazoles. Other method of intramolecular cyclization of diarylamines based on the reoxidation of the Pd(0) formed by Cu(OAc)2 , avoiding the use of stoichiometric amounts of Pd(OAc)2, gave thienocarbazoles in a moderate yield, including a ring A methoxylated compound. An attempt to combine palladium and copper catalyses in a “one pot” reaction of amination and intramolecular cyclization gave as major product a N-benzo[b]thiophene substituted carbazole and the required thienocarbazole in low yield.
publishDate 2002
dc.date.none.fl_str_mv 2002
2002-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://hdl.handle.net/1822/2255
url https://hdl.handle.net/1822/2255
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Ferreira, I. C. F. R., Queiroz, M.-J. R. P., & Kirsch, G. (2002, September). Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization. Tetrahedron. Elsevier BV. http://doi.org/10.1016/s0040-4020(02)00904-3
0040-4020
10.1016/S0040-4020(02)00904-3
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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