Chelation-assisted de-aryloxylative amination of 2-aryloxy quinolines: a new synthetic route to a key fragment of a bioactive PRMT5 inhibitor. Issue 20 (8th May 2018)

• Record Type: Journal Article
• Authors: Gupta, Aniket; Kumar, Jogendra; Bhadra, Sukalyan
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 20(2018)
• Page Start: 3716
• Page End: 3720
• Publication Date: 2018-05-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00911b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A copper catalysed regiospecific de-aryloxylative amination of O - or N -chelating group-functionalized 2-aryloxyquinolines constitutes a new route to access a 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.