Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway

Quinolines and isoquinolines were treated with Na2S2O8 in a mixture of methanol and water at 70 degrees C to form hydroxymethylated quinolines and isoquinolines in good to moderate yields, under transition-metal-free conditions. The formed hydroxymethyl group was smoothly converted into aldehyde, ester, amide, bromomethyl, (N,N-diethylamino)methyl, cyano, and tetrazole groups, in good yields.