Abstract
Synthesis of biologically active heterocyclic compounds via transition-metal-catalyzed direct transformation of an inactivated C–H bond into C–N bond is an emerging field in organic synthesis. Mostly these metal-catalyzed reactions are significantly introducing simple conversions and reduce reaction steps and cost. With this regards, this thesis described four new reactions for C–H bond functionalization and C–N bond formation via copper-catalyzed oxidative coupling reaction. In first chapter, we choose CuI and 2,2'-bipyridine to generate Cu(II)OH complex which can successfully proceeding sp2 C–H bond activation and intramolecular cyclization reactions to give acridone products by radical pathway. This reaction can be easily extended to various intermolecular cyclization, total synthesis of N-Methyl Toddaliopsin A and Arborinine with excellent yield. The 2nd chapter focuses on copper-catalyzed intermolecular oxidative C–N coupling reaction of acetophenone with amine hydrochloride salt. The catalytic system proceeds via superoxide radical subsequent acetophenone oxidation to give aryl glyoxal, and then last one react with amine to produce α-ketoamide. Chapter 3 deals with the combination of chapter 1 and 2. The reaction of Cu(II)OH complex with 2'-aminoacetophenone to give isatin via intramolecular direct oxidative C–H amination. This simple method offers an alternative, cheap path way to form isatin through C–N and C–O bond formation. The final chapter describes the copper-catalyzed oxidative amidation of alcohols with amine hydrochloride salts. This reaction condition provides an occasion for the synthesis of different aryl amides by less expensive catalyst.