Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes
Autor(a) principal: | |
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Data de Publicação: | 2004 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/2016 |
Resumo: | Several phenylacetylenes were coupled under Sonogashira cross coupling conditions with the methyl esters of N-(tert-butoxycarbonyl)-(E)-beta-bromo or beta, beta-dibromodehydroalanine to give respectively beta-substituted or beta,beta-bis-substituted dehydroalanines. The beta-substituted dehydroalanines were obtained in good to high yields (60-90%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol% Pd(PPh3)4, 2 mol% CuI 18 equiv. NEt3 in acetonitrile, 24h at rt) with maintenance of the stereochemistry. The beta,beta-bis-substituted dehydroalanines were in turn obtained in moderate to good yields (44-63%) requiring modified Sonogashira conditions (4 equiv. of the phenylacetylene,10 mol% PdCl2(PPh3)2, 20 mol% CuI, 1.4 equiv. Cs2CO3, 2h at reflux of acetonitrile). In the latter reactions some phenylacetylene dimer and the (E)-isomer of the mono substituted coupled products were also isolated in some extent. The Sonogashira products which were obtained from the 4-bromophenylacetylene were reacted with functionalized benzo[b]thiophenes under C-C or C-N palladium-catalyzed cross-coupling conditions. Preliminary fluorescence studies were performed for mono and disubstituted 4-aminophenylacetylenic dehydroamino acids and for the benzo[b]thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenesAmino acidsPhenylacetylenesSonogashira couplingPalladiumBenzo[b]thiophenesFluorescenceScience & TechnologySeveral phenylacetylenes were coupled under Sonogashira cross coupling conditions with the methyl esters of N-(tert-butoxycarbonyl)-(E)-beta-bromo or beta, beta-dibromodehydroalanine to give respectively beta-substituted or beta,beta-bis-substituted dehydroalanines. The beta-substituted dehydroalanines were obtained in good to high yields (60-90%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol% Pd(PPh3)4, 2 mol% CuI 18 equiv. NEt3 in acetonitrile, 24h at rt) with maintenance of the stereochemistry. The beta,beta-bis-substituted dehydroalanines were in turn obtained in moderate to good yields (44-63%) requiring modified Sonogashira conditions (4 equiv. of the phenylacetylene,10 mol% PdCl2(PPh3)2, 20 mol% CuI, 1.4 equiv. Cs2CO3, 2h at reflux of acetonitrile). In the latter reactions some phenylacetylene dimer and the (E)-isomer of the mono substituted coupled products were also isolated in some extent. The Sonogashira products which were obtained from the 4-bromophenylacetylene were reacted with functionalized benzo[b]thiophenes under C-C or C-N palladium-catalyzed cross-coupling conditions. Preliminary fluorescence studies were performed for mono and disubstituted 4-aminophenylacetylenic dehydroamino acids and for the benzo[b]thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes.Fundação para a Ciência e Tecnologia - POCTI/99/QUI/32689, SFRH/BD/4709/2001.WileyUniversidade do MinhoAbreu, Ana S.Ferreira, Paula M. T.Queiroz, Maria João R. P.Gatto, EmanuelaVenanzi, Mariano20042004-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/2016eng"European journal of organic chemistry". (2004) 3985-3991.1434-193X10.1002/ejoc.200400145info: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:RCAAP2023-07-21T12:15:46ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
title |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
spellingShingle |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes Abreu, Ana S. Amino acids Phenylacetylenes Sonogashira coupling Palladium Benzo[b]thiophenes Fluorescence Science & Technology |
title_short |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
title_full |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
title_fullStr |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
title_full_unstemmed |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
title_sort |
Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes |
author |
Abreu, Ana S. |
author_facet |
Abreu, Ana S. Ferreira, Paula M. T. Queiroz, Maria João R. P. Gatto, Emanuela Venanzi, Mariano |
author_role |
author |
author2 |
Ferreira, Paula M. T. Queiroz, Maria João R. P. Gatto, Emanuela Venanzi, Mariano |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Abreu, Ana S. Ferreira, Paula M. T. Queiroz, Maria João R. P. Gatto, Emanuela Venanzi, Mariano |
dc.subject.por.fl_str_mv |
Amino acids Phenylacetylenes Sonogashira coupling Palladium Benzo[b]thiophenes Fluorescence Science & Technology |
topic |
Amino acids Phenylacetylenes Sonogashira coupling Palladium Benzo[b]thiophenes Fluorescence Science & Technology |
description |
Several phenylacetylenes were coupled under Sonogashira cross coupling conditions with the methyl esters of N-(tert-butoxycarbonyl)-(E)-beta-bromo or beta, beta-dibromodehydroalanine to give respectively beta-substituted or beta,beta-bis-substituted dehydroalanines. The beta-substituted dehydroalanines were obtained in good to high yields (60-90%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol% Pd(PPh3)4, 2 mol% CuI 18 equiv. NEt3 in acetonitrile, 24h at rt) with maintenance of the stereochemistry. The beta,beta-bis-substituted dehydroalanines were in turn obtained in moderate to good yields (44-63%) requiring modified Sonogashira conditions (4 equiv. of the phenylacetylene,10 mol% PdCl2(PPh3)2, 20 mol% CuI, 1.4 equiv. Cs2CO3, 2h at reflux of acetonitrile). In the latter reactions some phenylacetylene dimer and the (E)-isomer of the mono substituted coupled products were also isolated in some extent. The Sonogashira products which were obtained from the 4-bromophenylacetylene were reacted with functionalized benzo[b]thiophenes under C-C or C-N palladium-catalyzed cross-coupling conditions. Preliminary fluorescence studies were performed for mono and disubstituted 4-aminophenylacetylenic dehydroamino acids and for the benzo[b]thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes. |
publishDate |
2004 |
dc.date.none.fl_str_mv |
2004 2004-01-01T00:00:00Z |
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 |
http://hdl.handle.net/1822/2016 |
url |
http://hdl.handle.net/1822/2016 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
"European journal of organic chemistry". (2004) 3985-3991. 1434-193X 10.1002/ejoc.200400145 |
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 |
Wiley |
publisher.none.fl_str_mv |
Wiley |
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 |
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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) |
repository.name.fl_str_mv |
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repository.mail.fl_str_mv |
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1777303717071028224 |