ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Mechanism of the Electroreduction of 3-Hydroxy-1,4-benzodiazepines at the Mercury Pool Electrode with a Controlled PotentialThe tranquilizer lorazepam [1c, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one] is reducible at the mercury pool electrode in acidic as well as in alkaline buffers. The reduction involves an e-c-e-mechanism. At first the 4,5-N=C double bond is reduced with consumption of two electrons, then follows elimination of water with formation of the aldimine 4c as the rate limiting step. This aldimine was isolated as its more stable tautomer 5c. Its reduction, with consumption of two further electrons, is the third step of the postulated e-c-e-mechanism.
Notes:
Der Tranquilizer Lorazepam [1c, 7-Chlor-5-(2-chlorphenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzo-diazepin-2-on] wird an der Hg-Pool-Elektrode sowohl in sauren als auch in alkalischen Puffern nach einem e-c-e-Mechanismus reduziert. Zunächst erfolgt 2elektronig die Reduktion der 4,5-N=C-Doppelbindung, danach als geschwindigkeitsbestimmender Schritt die Wasserabspaltung zum Aldimin 4c, das in Form seines stabileren Tautomeren 5c isoliert werden konnte, und abschließend dessen 2elektronige Reduktion.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19751081021
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