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

Dedicated to Professor Atta-ur-Rahman, PhD, Sc.D, N.I., FRS, FPAS, on the occasion of his 80th birthday

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

Key words

catalysis - cross-coupling - heterocycles - palladium - regioselectivity

Publication History

Received: 13 April 2022

Accepted after revision: 21 April 2022

Article published online:
09 June 2022

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