Synthesis 2016; 48(14): 2178-2190
DOI: 10.1055/s-0035-1562234
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© Georg Thieme Verlag Stuttgart · New York

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

Alexis Bontemps
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
,
Gaëlle Mariaule
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
b  Institut Curie, UMR CNRS 176, 26 rue d’Ulm, 75005 Paris, France   eMail: philippe.belmont@parisdescartes.fr
,
Stéphanie Desbène-Finck
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
,
Philippe Helissey
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
,
Sylviane Giorgi-Renault
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
,
Véronique Michelet*
c  PSL Research University, Chimie ParisTech-CNRS, Institut de Recherche de Chimie Paris, 11 rue P. et M. Curie, 75005 Paris, France   eMail: veronique.michelet@chimie-paristech.fr
,
Philippe Belmont*
a  Université Sorbonne Paris Cité and Université Paris Descartes, Faculté de Pharmacie de Paris, UMR CNRS 8638, 4 avenue de l’Observatoire, 75006 Paris, France
b  Institut Curie, UMR CNRS 176, 26 rue d’Ulm, 75005 Paris, France   eMail: philippe.belmont@parisdescartes.fr
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Publikationsverlauf

Received: 18. April 2016

Accepted: 21. April 2016

Publikationsdatum:
07. Juni 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.

Supporting Information

 
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