Trimethylsilylcyanation of N-[3-(2-Furyl)-2-propenylidene]trifluoromethylanilines

The addition of Me3SiCN to N-[3-(2-furyl)-2-propenylidene]trifluoromethylanilines, differing in the position of the CF3 group in the benzene ring and in the presence or absence of a methyl group in the heterocycle, was studied in the presence of aluminum bromide as catalyst. The direction of the process (1,2-addition in all cases) was determined, and certain other features of the reactions were discovered. A series of the corresponding unsaturated heterocyclic α-amino nitriles were synthesized. The molecular and crystal structures of one of them were determined by X-ray crystallographic analysis.