ISSN:
0947-3440
Keywords:
Electrochemistry
;
Anodic cyanation
;
1-Benzazepines
;
α-Aminonitriles
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α-Cyano-N-alkyl-1-benzazepines are obtained by electrochemical oxidation of various 1-benzazepines. Electrolyses are carried out in a flow cell, at a carbon felt anode in methanol; the supporting electrolyte is a mixture of lithium acetate and sodium cyanide. With 2,3,4,5-tetrahydrobenzazepines 2a-c and 5a-b, cyanation takes place either on the sidechain or on the seven-membered ring; with the latter, the 3-methyl substituted derivatives 5a-b, the reaction is stereospecific leading only to the trans-α-cyano compound. With dihydrobenzazepines 8a-b only ring cyanation occurs; the reaction is again stereospecific for 2,3-dihydro-1,3,5-trimethylbenzazepine (8a) but not for the 2,5-dihydro-1,3,5-trimethyl isomer (8b).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970137
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