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https://hdl.handle.net/1822/2016
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Campo DC | Valor | Idioma |
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dc.contributor.author | Abreu, Ana S. | - |
dc.contributor.author | Ferreira, Paula M. T. | - |
dc.contributor.author | Queiroz, Maria João R. P. | - |
dc.contributor.author | Gatto, Emanuela | - |
dc.contributor.author | Venanzi, Mariano | - |
dc.date.accessioned | 2005-06-08T10:05:31Z | - |
dc.date.available | 2005-06-08T10:05:31Z | - |
dc.date.issued | 2004 | - |
dc.identifier.citation | "European journal of organic chemistry". (2004) 3985-3991. | eng |
dc.identifier.issn | 1434-193X | por |
dc.identifier.uri | https://hdl.handle.net/1822/2016 | - |
dc.description.abstract | 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. | eng |
dc.description.sponsorship | Fundação para a Ciência e Tecnologia - POCTI/99/QUI/32689, SFRH/BD/4709/2001. | por |
dc.language.iso | eng | eng |
dc.publisher | Wiley | eng |
dc.rights | openAccess | eng |
dc.subject | Amino acids | eng |
dc.subject | Phenylacetylenes | eng |
dc.subject | Sonogashira coupling | eng |
dc.subject | Palladium | eng |
dc.subject | Benzo[b]thiophenes | eng |
dc.subject | Fluorescence | eng |
dc.title | Sonogashira cross-couplings of dehydroamino acid derivatives and phenylacetylenes | eng |
dc.type | article | eng |
dc.peerreviewed | yes | eng |
oaire.citationStartPage | 3985 | por |
oaire.citationEndPage | 3991 | por |
oaire.citationIssue | 19 | por |
dc.identifier.doi | 10.1002/ejoc.200400145 | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | European Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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EUJOC-MJQ.pdf | 166,19 kB | Adobe PDF | Ver/Abrir |