The C-N bonded aromatic compounds have demonstrated potential applications in energetic materials, polymers, agrochemicals, and medicinal chemistry. Developing improved methodologies for the streamlined and economical generation of C-N bonds is highly sought-after. In this study, an efficient strategy was developed to construct C-N bonded bis-heterocyclic compounds. A total of 26 substrates with different functional groups substituted azoles were selected to react with 1,3,4-trinitropyrazole. The results demonstrate that the C-N coupling reaction is predominantly influenced by the p