A Ru(II)-catalyzed facile and controllable protocol for C-H alkylation and spirocyclization of 2-arylquinoxalines with maleimides has been achieved under ambient air in high yields. Sequential ortho-C-H activation and C-annulation results in the formation of diverse polyheterocycles containing spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolidine]-2',5'-diones, which are of potent interest in medicinal chemistry. Mechanistic investigations suggest a reversible cleavage of the ortho-C-H bond in the turnover-limiting step.