ANODIC CYANATION OF N-SUBSTITUTED 1-BENZAZEPINES - SYNTHESIS OF THE CORRESPONDING ALPHA-AMINONITRILES

alpha-Cyano-N-alkyl-1-benzazepines are obtained by electrochemical oxi dation of various 1-benzazepines. Electrolyses are carried out in a fl ow cell, at a carbon felt anode in methanol; the supporting electrolyt e is a mixture of lithium acetate and sodium cyanide. With 2,3,4,5-tet rahydrobenzazepines 2a-c and 5a-b, cyanation takes place either on the side-chain or on the seven-membered ring; with the latter, the 3-meth yl substituted derivatives 5a-b, the reaction is stereospecific leadin g only to the trans-alpha-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-dihyd ro-1,3,5-trimethyl isomer (8b).