Reactions of N-1(2,2-dichloroalkylidene)amines with potassium cyanide: synthesis of β-chloro-α-cyanoenamines, α-chloroimidates and 2-amino-5-cyan
作者:Roland Verhé、Norbert De Kimpe、Laurent De Buyck、Marc Tilley、Niceas Schamp
DOI:10.1016/0040-4020(80)85035-6
日期:1980.1
Reaction of N-1(2,2-dichloroalkylidene)amines, prepared by chlorination of aliphatic aldimines with N-chlorosuccinimide, with excess of potassium cyanide in methanol gave β-chloro-α-cyanoenamines. When the reaction was carried out for a longer period, α-chloroimidates were isolated (except for N-t-Bu compounds). Reaction of the α-chloroaldimines with potassium cyanide in dimethylsulphoxide at 70° gave
通过用N-氯代琥珀酰亚胺氯化脂肪族醛亚胺而制备的N-1(2,2-二氯亚烷基)胺与甲醇中过量的氰化钾反应,得到β-氯代-α-氰基烯胺。当反应进行较长时间时,分离出α-氯亚氨酸盐(Nt-Bu化合物除外)。α-氯代亚胺与氰化钾在二甲基亚砜中在70°下反应生成1,2-二氰基烯胺,而在120°下通过1,3-二氰基烯胺生成2-氨基-5-氰基吡咯。讨论了反应机理。