An expedient synthesis of poly-substituted 1-arylisoquinolines from δ-ketonitriles via indium-mediated Barbier reaction protocol

We developed an efficient synthetic strategy of poly-substituted 1-arylisoquinolines via an indium-mediated Barbier type allylation from delta-ketonitriles. Initial attack of allylindium species Occurred at the nitrile group selectively to form the enamine intermediate, which reacted with the ketone group intramolecularly to furnish the isoquinolines. (C) 2009 Elsevier Ltd All rights reserved.