Abstract
AbstractThe anodic behavior of the cardiotonic drug 3‐amino‐5‐(pyrid‐4‐yl)‐1,2‐dihydropyrid‐2‐one 1 and of 6 compounds with similar structure was investigated at platinum and vitreous carbon electrodes in acetonitrile and in aqueous medium. Caused by the 3‐amino group 1 is oxidized at a relatively small oxidation potential in an irreversible two‐electron process. Depending on the addition of a strong base or a strong acid the oxidation potential vs. SCE in acetonitrile is −0.08 V (anion), +0.66 V (neutral compound), +0.93 V (monocation) or +1.15 V (dication). In H2O a strong decrease of the oxidation potential with increasing pH was found as a reason for the sensitivity of 1 against oxygen in alkaline solution. The anodic oxidation of 3‐dimethylamino‐5‐(pyrid‐4‐yl)‐1, 2‐dihydro‐pyrid‐2‐one 3 in 0.1 m H2SO4 leads to 5‐(pyrid‐4‐yl)‐piperidine‐2,3,6‐trione 9a or 5‐(pyrid‐4‐yl)‐piperidine‐2,3,4‐trione 9b, which is also the oxidation product of 1 at small concentration. At high concentration of 1 coupling reactions at the 3‐amino‐group lead to dimeric products, which could not be identified.
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