Regioselective Synthesis of 3‐Substituted Isocoumarin‐1‐imines via Palladium‐Catalyzed Denitrogenative Transannulation of 1,2,3‐Benzotriazin‐4(3<i>H</i>)‐ones and Terminal Alkynes
Madasamy Hari Balakrishnan, Popuri Sureshbabu, Ramaraju Korivi, Subramaniyan Mannathan
Abstract
A palladium-catalyzed denitrogenative transannulation strategy to access various 3-substituted isocoumarin-1-imine frameworks using 1,2,3-benzotriazin-4(3H)-ones and terminal alkynes is described. The reaction is highly regioselective and tolerates a wide range of functional groups. The reaction is believed to proceed via a five-membered palladacycle intermediate extruding environmentally benign molecular nitrogen as a by-product. The utility of this method was showcased through the one-pot synthesis of biologically relevant 3-substituted isocoumarin scaffolds.
Topics & Concepts
IsocoumarinRegioselectivityIminePalladiumChemistryCatalysisIsocoumarinsCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Biological ActivitySynthesis and Catalytic Reactions