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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
Visible Light Mediated Aryl Migration by Homolytic C-N Cleavage of Aryl Amines
Dirk Alpers1, Kevin P Cole2, Corey R J Stephenson1
1Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109, USA.
Abstract:
The photocatalytic preparation of aminoalkylated heteroarenes from haloalkylamides via a 1,4-aryl migration from nitrogen to carbon, conceptually analogous to a radical Smiles rearrangement, is reported. This method enables the substitution of amino groups in heteroaromatic compounds with aminoalkyl motifs under mild, iridium(III)-mediated photoredox conditions. It provides rapid access to thienoazepinone, a pharmacophore present in multiple drug candidates for potential treatment of different conditions, including inflammation and psychotic disorders.
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