Reactions of nitric oxide (NO) with amines in organic solvents were st
udied using Hantzsch dihydropyridines and aromatic primary amines as s
ubstrates. Hantzsch dihydropyridines are readily oxidized by nitric ox
ide to give the corresponding pyridines in quantitative yields. The ad
dition of oxygen accelerates the reaction rate considerably. On the ot
her hand, aromatic primary amines give deaminated products by the reac
tion with nitric oxide only in the presence of oxygen in ethereal solv
ents or chloroform.