Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives

Detalhes bibliográficos
Autor(a) principal: Abreu, Ana S.
Data de Publicação: 2003
Outros Autores: Silva, Natália O., Ferreira, Paula M. T., Queiroz, Maria João R. P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/2057
Resumo: The methyl ester of tert-butyloxycarbonyl-beta,beta-dibromodehydroalanine was obtained in a one pot procedure from bis-(N-tert-butyloxycarbonyl)dehydroalanine. The former was reacted with several boronic benzo[b]thiophene acids under Suzuki cross coupling conditions, to give new beta,beta-bis-(benzo[b]thienyl)dehydroalanines in high yields. These compounds were cyclized to pyrrole derivatives by treatment with Pd(OAc)2 and Cu(OAc)2 in DMF.
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spelling Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivativesBeta,beta-dibromodehydroalanineBeta,beta-bis-(benzo[b]thienyldehydroalanineSuzuki cross couplingPyrrole derivativesβ,β-bis-(benzo[b]thienyl) dehydroalanineβ,β-dibromodehydroalanineScience & TechnologyThe methyl ester of tert-butyloxycarbonyl-beta,beta-dibromodehydroalanine was obtained in a one pot procedure from bis-(N-tert-butyloxycarbonyl)dehydroalanine. The former was reacted with several boronic benzo[b]thiophene acids under Suzuki cross coupling conditions, to give new beta,beta-bis-(benzo[b]thienyl)dehydroalanines in high yields. These compounds were cyclized to pyrrole derivatives by treatment with Pd(OAc)2 and Cu(OAc)2 in DMF.We wish to thank the Foundation for Science and Technology (Portugal) for financial support through project POCTI/1999/QUI/32689 (also support of N.O. Silva) and through SFRH/BD/4709/2001, PhD financial support of A.S. Abreu.ElsevierUniversidade do MinhoAbreu, Ana S.Silva, Natália O.Ferreira, Paula M. T.Queiroz, Maria João R. P.20032003-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/2057engAbreu, A. S., Silva, N. O., Ferreira, P. M. T., & Queiroz, M.-J. R. P. (2003, April). Synthesis and intramolecular cyclization of novel β,β-bis-(benzo[b]thienyl)dehydroalanine derivatives. Tetrahedron Letters. Elsevier BV. http://doi.org/10.1016/s0040-4039(03)00564-10040-403910.1016/S0040-4039(03)00564-1info: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:RCAAP2023-07-21T12:47:39ZPortal AgregadorONG
dc.title.none.fl_str_mv Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
title Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
spellingShingle Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
Abreu, Ana S.
Beta,beta-dibromodehydroalanine
Beta,beta-bis-(benzo[b]thienyldehydroalanine
Suzuki cross coupling
Pyrrole derivatives
β,β-bis-(benzo[b]thienyl) dehydroalanine
β,β-dibromodehydroalanine
Science & Technology
title_short Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
title_full Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
title_fullStr Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
title_full_unstemmed Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
title_sort Synthesis and intramolecular cyclization of novel beta,beta-bis(benzo[b]thienyl)dehydroalanine derivatives
author Abreu, Ana S.
author_facet Abreu, Ana S.
Silva, Natália O.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
author_role author
author2 Silva, Natália O.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Abreu, Ana S.
Silva, Natália O.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
dc.subject.por.fl_str_mv Beta,beta-dibromodehydroalanine
Beta,beta-bis-(benzo[b]thienyldehydroalanine
Suzuki cross coupling
Pyrrole derivatives
β,β-bis-(benzo[b]thienyl) dehydroalanine
β,β-dibromodehydroalanine
Science & Technology
topic Beta,beta-dibromodehydroalanine
Beta,beta-bis-(benzo[b]thienyldehydroalanine
Suzuki cross coupling
Pyrrole derivatives
β,β-bis-(benzo[b]thienyl) dehydroalanine
β,β-dibromodehydroalanine
Science & Technology
description The methyl ester of tert-butyloxycarbonyl-beta,beta-dibromodehydroalanine was obtained in a one pot procedure from bis-(N-tert-butyloxycarbonyl)dehydroalanine. The former was reacted with several boronic benzo[b]thiophene acids under Suzuki cross coupling conditions, to give new beta,beta-bis-(benzo[b]thienyl)dehydroalanines in high yields. These compounds were cyclized to pyrrole derivatives by treatment with Pd(OAc)2 and Cu(OAc)2 in DMF.
publishDate 2003
dc.date.none.fl_str_mv 2003
2003-01-01T00:00:00Z
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/1822/2057
url https://hdl.handle.net/1822/2057
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Abreu, A. S., Silva, N. O., Ferreira, P. M. T., & Queiroz, M.-J. R. P. (2003, April). Synthesis and intramolecular cyclization of novel β,β-bis-(benzo[b]thienyl)dehydroalanine derivatives. Tetrahedron Letters. Elsevier BV. http://doi.org/10.1016/s0040-4039(03)00564-1
0040-4039
10.1016/S0040-4039(03)00564-1
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
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)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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repository.mail.fl_str_mv
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