Biblioteca Digital do Instituto Politécnico de Bragança   Instituto Politécnico de Bragança

Biblioteca Digital do IPB >
Escola Superior Agrária >
Biologia e Biotecnologia >
BB - Artigos em Revistas Indexados ao ISI/Scopus >

Please use this identifier to cite or link to this item: http://hdl.handle.net/10198/823

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
Autor: Abreu, Ana S.
Ferreira, Paula M.T.
Queiroz, Maria João R.P.
Ferreira, Isabel C.F.R.
Calhelha, Ricardo C.
Estevinho, Leticia M.
Palavras-chave: Dehydrophenylalanines
Benzothiophenes
Borylation
Suzuki coupling
Cyclization
Indoles
Fluorescence
Antimicrobial activity
Issue Date: 2005
Editora: Wiley Interscience
Citação: European Journal of Organic Chemistry. ISSN 1434-193X. 2005:14 (2005) p. 2951-2957
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.
URI: http://hdl.handle.net/10198/823
ISSN: 1434-193X
Appears in Collections:BB - Artigos em Revistas Indexados ao ISI/Scopus

Files in This Item:

File Description SizeFormat
EJOC.pdf132,6 kBAdobe PDFView/Open

Please give feedback about this item
Statistics
FacebookTwitterDeliciousLinkedInDiggGoogle BookmarksMySpaceOrkut
Formato BibTex mendeley Endnote Logotipo do DeGóis 

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 


© Instituto Politécnico de Bragança - Biblioteca Digital - Feedback - Statistics
Promotores do RCAAP   Financiadores do RCAAP

Fundação para a Ciência e a Tecnologia Universidade do Minho   Governo Português Ministério da Educação e Ciência PO Sociedade do Conhecimento (POSC) Portal oficial da União Europeia