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Palladium-catalyzed amination and cyclization to heteroannellated indoles and carbazoles IPB - Escola Superior Agrária
Ferreira, Isabel C.F.R.; Queiroz, Maria João R.P.; Kirsch, Gilbert.
New ortho-bromodiarylamines in the benzo[b]thiophene series were prepared by palladium-catalyzed amination, either in the benzene or in the thiophene ring. These were submitted to palladium-catalyzed cyclization, under different required conditions, to give several differently substituted thieno[3,2-c] or [2,3-b]carbazoles and indolo[3,2-b]benzo[b]thiophenes. This constitutes a novel synthetic route to both tetracyclic systems
Tipo: Article Palavras-chave: Palladium; Amination; Ortho-bromodiarylamines; Cyclization.
Ano: 2003 URL: http://hdl.handle.net/10198/817
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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 IPB - Escola Superior Agrária
Abreu, Ana S.; Ferreira, Paula M.T.; Queiroz, Maria João R.P.; Ferreira, Isabel C.F.R.; Calhelha, Ricardo C.; Estevinho, Leticia M..
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...
Tipo: Article Palavras-chave: Dehydrophenylalanines; Benzothiophenes; Borylation; Suzuki coupling; Cyclization; Indoles; Fluorescence; Antimicrobial activity.
Ano: 2005 URL: http://hdl.handle.net/10198/823
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