Boron Trifluoride‐Promoted Indium(III) Triflate‐Catalyzed Sequential One‐Pot Synthesis of (1,2‐Diaryl‐2‐oxoethyl)malonates from trans‐2‐Aryl‐3‐nitrocyclopropane‐1,1‐dicarboxylates and Activated Arenes

Abstract

AbstractA sequential one‐pot synthesis of Michael adducts of aroylmethylidenemalonates with activated aromatics is described. The method involves treatment of trans‐2‐aryl‐3‐nitro‐cyclopropane‐1,1‐dicarboxylates with boron trifluoride etherate to form aroylmethylidenemalonates in situ and then addition of activated aromatics such as indoles, carbazole, pyrrole, thiophenes, methoxybenzenes and benzodioxole followed by a catalytic amount of indium(III) triflate to the same reaction vessel. To prove the synthetic potential of the resulting Michael adducts, one of the adducts was transformed into a pharmaceutically interesting dihydropyridazinone derivative.magnified image