Transition-metal-free access to biologically important scaffolds via novel C–C and C–X bond formations using aryne chemistry

Abstract

The present thesis demonstrates the importance of aryne in the construction of C–C, C–S, and C–N bonds, which result in the synthesis of the biologically important scaffolds. Chapter 1 presents the introduction of aryne and its mode of reactivity especially leading to the difunctionalization of arenes. It comprises insertion, pericyclic, annulation and multicomponent reactions of aryne and their representative examples. Chapter 2 deals with difunctionalization of aryne to form sulfones and xanthones, which is further divided into two sections. Section 1 presents the transition-metal-free synthesis of sulfones using aryne chemistry. We were able to synthesize diaryl as well as alkyl aryl sulfones in excellent yields. Section 2 reveals the effort towards the total synthesis of diversonol natural product. Chapter 3 demonstrates the novel process for the synthesis of varyingly substituted oxindolylidene acetates in good yields. This method has been further extended to the one-pot synthesis of spiroxindolopyrrolidones. Chapter 4 describes the utilization of aryne in the general synthesis of octahydroquinoline scaffold in a stereoselective manner.