Synthesis of Polyfunctionalized Pyrroles via a Tandem Reaction of Michael Addition and Intramolecular Cyanide-Mediated Nitrile-to-Nitrile Condensation

A new approach for the synthesis
of tetrasubstituted/functionalized
NH-pyrroles from gem-diactivated acrylonitriles and
TMSCN has been developed. The strategy utilizes the generation of vic-dinitrile via Michael addition and cyanide-mediated
nitrile-to-nitrile cyclocondensation, which proceed in tandem guided
by manifold roles of “CN”. An extended application to
the production of fused pyrrole has also been realized.