Several 2′-functionalized 3-arylisoquinolines in different oxidation stages have been prepared. Fremy's salt or I2/NaAcO oxidation of 2′-functionalized 3- aryltetrahydroisociuinolines always stops at the 3, 4-dihydroisquinoline stage; however, better yields and shorter reaction times are obtained with iodine. Air/KOH/DMSO oxidation of 3, 4-dihydroisoquinolines furnished the aromatic derivatives with concomitant cleavage of ...