A new method for the synthesis of perfluoroalkylated derivatives of γ-carboline and
pyrrolopyrazine was elaborated. Pictet–Spengler reaction of isotryptamine and 2-(pyrrol-1-yl)ethanamine
with trifluoromethylated carbonyls and 2-perfluoroalkyl-substituted five-, six-, and
seven-membered cyclic imines was studied. It was found that this approach opens efficient
access to a family of alkaloid-like compounds bearing a CF3 or C2F5 group in the structure. In the case of the iso-Pictet–Spengler reaction with 2-perfluoroalkyl-substituted
cyclic imines, a series of γ-carbolines bearing an aminoalkyl group were prepared.
Key words
iso-Pictet–Spengler reaction - isotryptamine - fluorine - trifluoromethyl - carboline
- imine
