Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide Double Insertion Reaction with Terminal Alkynes and Water

Abstract

With the combination of Pd(dppf)Cl₂ and Cu(OAc)₂, a variety of 5-iminopyrrolones were synthesized in moderate to good yields from terminal alkynes, isocyanide, and water via isocyanide double insertion and cycloaddition reaction. A plausible reaction mechanism for this process is depicted. Furthermore, selected compounds 3c, 3e, and 3h exhibited good activities against HepG2 (human liver cancer), NCI-H460 (human lung cancer), and SK-OV-3 (human ovarian cancer) cell lines with IC₅₀ values in the range of 10.63-22.63 μmol L^-1.