Synthesis of Polysubstituted Pyrroles through the Tandem 1,3-Addition/5-endo-dig Cyclization of 1-(1-Alkynyl)cyclopropyl Imines

Cyclopropyl-tethered 3-alkynyl imines react with polarized-covalent-bond-containing compounds to give polyfunctionalized pyrroles. This provides a mild and effective method for the simultaneous introduction of halogen, chalcogen, or hydrogen groups to the 3-position of the pyrrole ring, together with the incorporation of halogen, azide, or alkoxy/aryloxy groups into the ethyl side-chain.