ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 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.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290507
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