Issue 20, 2018

Chelation-assisted de-aryloxylative amination of 2-aryloxy quinolines: a new synthetic route to a key fragment of a bioactive PRMT5 inhibitor

Abstract

A highly regioselective de-aryloxylative amination of O- or N-chelating group-functionalized 2-aryloxy quinolines has been accomplished by means of a copper catalyst. The chelating functional groups of the substrate play a crucial role in directing the C-2-selective amination process, which proceeds through a novel aromatic nucleophilic substitution of the aryloxy group. The methodology provides expedient access to an important class of functionalized 2-aminoquinolines (up to 88% isolated yield) and was successfully applied for the synthesis of a key fragment of an important bioactive PRMT5 inhibitor.

Graphical abstract: Chelation-assisted de-aryloxylative amination of 2-aryloxy quinolines: a new synthetic route to a key fragment of a bioactive PRMT5 inhibitor

Supplementary files

Article information

Article type
Communication
Submitted
18 Apr 2018
Accepted
02 May 2018
First published
08 May 2018

Org. Biomol. Chem., 2018,16, 3716-3720

Chelation-assisted de-aryloxylative amination of 2-aryloxy quinolines: a new synthetic route to a key fragment of a bioactive PRMT5 inhibitor

A. Gupta, J. Kumar and S. Bhadra, Org. Biomol. Chem., 2018, 16, 3716 DOI: 10.1039/C8OB00911B

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