A reductive amidation of triazine esters with nitroarenes
by using
cheap iron as a reducing metal in the presence of TMSCl in DMF was
developed. The reactions proceeded efficiently under transition metal-free
conditions to give the corresponding amides in moderate to good yields
with good functional group compatibility. Preliminary mechanistic
investigations indicated that nitrosobenzene, N-phenyl
hydroxylamine, azoxybenzene, azobenzene, aniline, and N-arylformamide possibly served as the intermediates of the reaction.