Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines

Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines

Abstract A silver trifluoromethanesulfonate catalyzed efficient access to the indolylpyranoquinoline scaffold is reported. Starting from 2-alkynylquinoline-3-carbaldehyde units with various substitution patterns on the quinoline and alkynyl parts, the use of silver trifluoromethanesulfonate (10 mol%...

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Veröffentlicht in:Synthesis (Stuttgart) 2016-07, Vol.48 (14), p.2178-2190
Hauptverfasser: Bontemps, Alexis, Mariaule, Gaëlle, Desbène-Finck, Stéphanie, Helissey, Philippe, Giorgi-Renault, Sylviane, Michelet, Véronique, Belmont, Philippe
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container_end_page 2190
container_issue 14
container_start_page 2178
container_title Synthesis (Stuttgart)
container_volume 48
creator Bontemps, Alexis
Mariaule, Gaëlle
Desbène-Finck, Stéphanie
Helissey, Philippe
Giorgi-Renault, Sylviane
Michelet, Véronique
Belmont, Philippe
description Abstract A silver trifluoromethanesulfonate catalyzed efficient access to the indolylpyranoquinoline scaffold is reported. Starting from 2-alkynylquinoline-3-carbaldehyde units with various substitution patterns on the quinoline and alkynyl parts, the use of silver trifluoromethanesulfonate (10 mol%) in 1,2-dichloroethane allowed a domino hydroarylation/cycloisomerization reaction, generating (hetero)aryl-functionalized pyranoquinolines. The heteroarenes that were used are N -methylindole (18 compounds, 67–100%), indole, and 2-methylindole (4 compounds, 36–89%), and the reaction was also compatible to a lesser extent with arenes such as pyrroles (5 compounds, 43–90%), 1,3,5-trimethoxybenzene, and 3-methylbenzofuran.
doi_str_mv 10.1055/s-0035-1562234
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title Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines
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