Anodic Cyanation ofN-Substituted 1-Benzazepines: Synthesis of the Corresponding α-Aminonitriles

✍ Scribed by Michel, Sébastien ;Le Gall, Erwan ;Hurvois, Jean-Pierre ;Moinet, Claude ;Tallec, André ;Uriac, Philippe ;Toupet, Loic

• Book ID: 102901211
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 852 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970137

✦ Synopsis

Abstract

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).