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Provedor de dados:  IPB - Escola Superior Agrária
País:  Portugal
Título:  Synthesis of β - benzo[b]thienyldehydrophenylalanine derivatives by one-pot palladium-catalyzed borylation and suzuki coupling (BSC) and metal-assisted intramolecular cyclization: studies of fluorescence and antimicrobial activity
Autores:  Abreu, Ana S.
Ferreira, Paula M.T.
Queiroz, Maria João R.P.
Ferreira, Isabel C.F.R.
Calhelha, Ricardo C.
Estevinho, Leticia M.
Data:  2008-09-12
Ano:  2005
Palavras-chave:  Dehydrophenylalanines
Benzothiophenes
Borylation
Suzuki coupling
Cyclization
Indoles
Fluorescence
Antimicrobial activity
Resumo:  Palladium-catalyzed borylation and Suzuki coupling (BSC) in a one-pot procedure was successfully applied to the synthesis of several β-substituted dehydrophenylalanines in the benzo[b]thiophene series, with the stereochemistry of the starting materials being maintained. Bromobenzo[b]thiophenes bearing an ortho EDG (OMe or Me) were used as the components to be borylated with pinacolborane, whilst pure stereoisomers of β-bromodehydrophenylalanines were used as the other Suzuki coupling components. Treatment of the obtained methyl ester of (Z)-N-(tert-butoxycarbonyl)-β- (2,3,5-trimethylbenzo[b]thien-6-yl)dehydrophenylalanine with Pd(OAc)2 and Cu(OAc)2 in DMF at 160 °C gave two in dole derivatives (1:3), the major product resulting from isomerization and cyclization and the minor product resulting from direct cyclization (thienoindole). Carrying out the reaction at 100 °C gave the same products in similar amounts. Use of the methyl ester of (Z)-N-(tert-butoxycarbonyl)-β- (2,3,7-trimethylbenzo[b]thien-6-yl)dehydrophenylalanine as starting material gave only one product, resulting from isomerization and cyclization at 100 °C. Two of the cyclized compounds were subjected to fluorescence studies; the thienoindole could be useful as a fluorescent probe. Preliminary studies of antimicrobial activity were performed on the precursors and on the cyclized products.
Tipo:  Article
Idioma:  Inglês
Identificador:  European Journal of Organic Chemistry. ISSN 1434-193X. 2005:14 (2005) p. 2951-2957

1434-193X

http://hdl.handle.net/10198/823
Editor:  Wiley Interscience
Direitos:  open access
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