Synthesis of Nitrogen Heterocycles by Domino C–N Coupling/Hydroamination Reactions

Abstract The present article presents a personalized Account on the synthesis of nitrogen heterocycles by domino C–N coupling/hydroamination reactions and related processes. The starting materials, 2-alkynyl-1-halohetarenes, are regioselectively available by Sonogashira reactions of various 1,2-dihalogenated heterocycles, such as thiophenes, benzothiophenes, furans and benzofurans, pyridines, quinolines, pyrimidines, and other ring systems. More complex products are formed by domino C–N coupling/hydroamination/C–H arylation reactions of 2-alkynyl-1-halohetarenes with 2-bromoanilines. In these reactions, not only two, but three bonds are formed in one step. In many cases, the products constitute new heterocyclic core structures and show interesting pharmacological or fluorescence properties. 1 Introduction 2 Domino C–N Coupling/Hydroamination Reactions 3 Domino C–N Coupling/Hydroamination/C–H Arylation Reactions 4 Conclusions