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

Autor:	Alexis Bontemps, Philippe Belmont, Philippe Helissey, Véronique Michelet, Stéphanie Desbène-Finck, Sylviane Giorgi-Renault, Gaëlle Mariaule
Rok vydání:	2016
Předmět:	Indole test 010405 organic chemistry Organic Chemistry Quinoline 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Domino 0104 chemical sciences chemistry.chemical_compound Cycloisomerization chemistry Cascade reaction Organic chemistry Silver trifluoromethanesulfonate
Zdroj:	Synthesis. 48:2178-2190
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0035-1562234
Popis:	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.
Databáze:	OpenAIRE
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