Sequential hydroarylation/Prins cyclization: an efficient strategy for the synthesis of angularly fused tetrahydro-2H-pyrano[3,4-c]quinolines?

RSC Advances Pub Date: 2016-11-28 DOI: 10.1039/C6RA21375H

Abstract

Various aldehydes undergo a smooth cascade cyclization with N-(5-hydroxypent-2-yn-1-yl)-4-methyl-N-phenylbenzenesulfonamide in the presence of 10 mol% Ph3PAuCl/AgSbF6/In(OTf)3 to furnish the corresponding tetrahydro-2H-pyrano[3,4-c]quinoline derivatives in good yields with high selectivity. This is the first report on the synthesis of tetrahydro-2H-pyrano[3,4-c]quinolines through a tandem hydroarylation/Prins cyclization process.

Graphical abstract: Sequential hydroarylation/Prins cyclization: an efficient strategy for the synthesis of angularly fused tetrahydro-2H-pyrano[3,4-c]quinolines
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