One-pot synthesis of novel polysubstituted 1,1′-phenylene-bipyrrole via the double [3+2] cycloaddition reaction

The novel polysubstituted 1,1′-phenylene-bipyrrole compounds were synthesized by the double [3+2] cycloaddition-extrusion reactions of N,N′-phenylene-bimünchnones and dimethyl acetylenedicarboxylate in dry toluene at 80 °C for 24 h. Bimünchnones were prepared successfully by cyclodehydration reactions of N,N′-biacyl-N,N′-(1,4-phenylene)-bis(2-arylglycine) with N,N′-diisopropylcarbodiimide in dry toluene at 0–5 °C for 1.5 h. The structures of the products were characterized on the basis of spectral data.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide