The development of an efficient process that produces bioactive medium-sized N-heterocyclic scaffolds from 2-substituted anilines using either iodosobenzene or (bis(trifluoroacetoxy)iodo)-benzene is reported. The tether between the sulfonamide and the aryl group can be varied to access dihydroacridine-, dibenzazepine-, or dibenzazocine scaffolds. While substitution on the aniline portion is limited to electron-neutral-or electron-poor groups, a broader range of functional groups are tolerated on the ortho-aryl substituent and site selective CÀ NAr bond formation can be achieved. Preliminary mechanistic investigations suggest that mediumring formation occurs via radical reactive intermediates.