One‐Pot Synthesis of Functionalized Isoindolinones and Their Bis(isoindolinone)ethane Derivatives

Abstract Highly efficient one‐pot synthesis of a series of substituted 3‐methylene‐isoindolinones ( 3 a – x ), bis(isoindolinone)ethanes ( 4 a – d ) and 3‐hydroxy‐isoindolinones ( 6 a – h ) derivatives is portrayed from easily accessible starting materials such as 2‐cyanobenzaldehydes ( 1 a – h ) and different aryl/heteroaryl methyl ketones ( 2 a – k ). The structure of Z‐isomer of 3‐methylene‐isoindolinone 3 x was confirmed by single crystal X‐ray analysis. The reaction mechanism studies by control experiments and using O 18 ‐labelled water revealed that the reaction was initiated by attack of a conjugate base of aryl/heteroaryl methyl ketones ( 2 a – k ) to aldehyde group of 1 a – h followed by intramolecular oxidative cyclization involving nitrile functionality to furnish isoindolinone derivatives in good to excellent yields.