Applications Of Isocyanide Insertion In The Synthesis Of Alkynones And Nitrogen-Containing Heterocycles

Since the pioneering work of Passarini and Ugi, the utility of nucleophilicity andelectrophilicity of isocyanides in multicomponent reactions (MCRs) has been widelyexplored. In the past decades, a new application of isocyanides as versatile C1buildingblocks instead of carbon monoxide in transition-metal catalysis has been attracting moreattention. Numerous literatures involving isocyanide insertion have been reported,mainly focusing on the carbonylative or imidoylative reactions of nitrogen and oxygennucleophiles. Herein, the thesis reports transition-metal catalyzed coupling of carbon andnitrogen nucleophiles with isocyanide for the formation of C-C and C-N bonds.The first part (Chapter2) centres on the synthesis of alkynones. It describes asimple and efficient palladium-catalyzed carbonylative Sonogashira coupling viatert-butyl isocyanide insertion for the synthesis of alkynyl imines and subsequentlysimple hydrolysis to afford alkynones, which demonstrates the utility of isocyanides inintermolecular C-C bond construction.The second part (Chapters3and4) centres on the synthesis of nitrogen-containingheterocycles, including palladium-catalyzed synthesis of6H-isoindolo[2,1-a]indol-6-ones and indenoindolones and nickel-catalyzed synthesis of imine derivatives ofbenzimidazo[2,1-a]isoindolones via isocyanide insertion. The former demonstrates theutility of isocyanides in C–N or C–C bond construction. The latter reveals the highreactivity of nickel catalyst in isocyanide insertion again. The products are undergoinganticancer activity study.