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

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

Automated summary

The present article discusses the personalized Account on the synthesis of nitrogen heterocycles through domino C-N coupling/hydroamination reactions and related processes. The starting materials, 2-alkynyl-1-halohetarenes, are obtained regioselectively by Sonogashira reactions of various 1,2-dihalogenated heterocycles. The formation of more complex products is achieved through domino C-N coupling/hydroamination/C-H arylation reactions. These reactions result in the formation of new heterocyclic core structures with interesting pharmacological or fluorescence properties.