Pictet–Spengler Synthesis of Perfluoroalkylated Tetrahydro-γ-carbolines and Tetrahydropyrrolopyrazines

Abstract

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

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