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Synthesis 2016; 48(14): 2178-2190
DOI: 10.1055/s-0035-1562234
DOI: 10.1055/s-0035-1562234
feature
Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines
Further Information
Publication History
Received: 18 April 2016
Accepted: 21 April 2016
Publication Date:
07 June 2016 (online)
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.
Key words
-
hydroarylation -
silver -
cycloisomerization -
indolylpyranoquinolines -
domino reaction -
cyclofunctionalization
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562234.
- Supporting Information
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