Efficient Heteroannulation Route for the Synthesis of Isoindoles and Pyrroles

Significance

Reported is the synthesis of isoindoles and pyrroles through the reaction of primary amines with formyl alkenyl acrylonitriles or formyl alkenyl acrylic esters which were in turn prepared by a Heck reaction of formyl alkenyl bromides. The cyclization may obviously proceed through either initial condensation or Michael addition. Reaction using a secondary amine instead of a primary amine produced a product consistent with a mechanism involving condensation as the first step.