ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrochemistry of Organic Cations. V. Synthesis of 3, 10-Diaza-tricyclo[5.3.1.12,6]dodeca-4,8-diene Derivatives by a Two-Step Electrochemical Reduction of Pyridinium IonsA series of 1-substituted 2,4,6-trimethylpyridinium ions 1a-1k is cathodically dimerized in alkaline medium. The bis-[1,4-dihydropyridinyl-(4)]-derivatives 2 obtained or their isomers 4 are submitted to a further cathodic reduction in aqueous acetic acid at mercury or lead electrodes to form 3,10-diaza-tricyclo[5.3.1.12,6]dodeca-4,8-dienes 6 by an intramolecular coupling reaction between the 2- and 2′-carbon atoms of the dihydropyridine rings. Depending on R1 the yields of 6 are 65-80% (R1 = alkyl or substituted alkyl) or 3,5-5% (R1 = aryl).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290416
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