Cyanoferrocenylacetylene hydroamination and reaction with 1-methylimidazole

Author: natia batiashvili
Keywords: cyanoacetylene, ferrocenes, hydroamination, 1-methylimidazole.
Annotation:

An effective synthesis of cyanoferrocenylacetylene is developed which includes dehydration of 3-ferrocenyl-3-chloroacrolein oxime with cyanuric chloride and subsequent dehydrohalogenation of the formed 3-ferrocenyl-3-chloroacrylonitrile with potassium hydroxide in tert-butyl alcohol. Cyanoferrocenylacetylene reacts smoothly with morpholine to give the hydroamination product –corresponding enaminonitrile. 1-Methylimidazole reacts with cyanoferrocenylacetylene at room temperature to afford 1-methyl-2-(2-cyano-1-ferrocenylethenyl)imidazole. The carbene intermediate of this reaction can be trapped as the corresponding 2-thione by the interaction with sulfur.