Functionalized 2,3-Bipyrroles and Pyrrolo[1,2-c]imidazoles from Acylethynylpyrroles and Tosylmethylisocyanide

An efficient method for the synthesis of pharmaceutically prospective but still rare functionalized 2,3 '-bipyrroles (in up to 80% yield) by the cycloaddition of easily available acylethynylpyrroles with tosylmethylisocyanide (TosMIC) has been developed. The reaction proceeds under reflux (1 h) in the KOH/THF system. In the t-BuONa/THF system, TosMIC acts in two directions: along with 2,3 '-bipyrroles, the unexpected formation of pyrrolo[1,2-c]imidazoles is also observed (products ratio similar to 1:1).