Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels–Alder Reaction Employing Two Dienophiles
Muhammad Saeed Akhtar, Yong Rok Lee
Abstract
An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.
Topics & Concepts
PhthalimidesPhthalimideCycloadditionChemistryImideDiels–Alder reactionCatalysisCombinatorial chemistryReaction conditionsOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms