Two radical-mediated cascade couplings of N-alkyl-N-methacryloylbenzamides with different ethers and arylsulfonohydrazides to generate ether- and aryisulfonyl-substituted isoquinoline-1,3(2H,4H)-dione derivatives were developed. Both casccades proceeded via initially triggered functionalization of the alkene functions of the N-alkyl-N-methacryloyl benzamides, followed by ortho radical cydizations onto the aromatic ring to give isoquinoline-1,3(2H,4H)-dione derivatives in good yields. These highly functionalized drug-like molecules will be valuable in drug discovery in the future. [ABSTRACT FROM AUTHOR]