Mechanochemical Synthesis of 1,2,4-Triazoles via a [3+2] Cycloaddition of Azinium-N-Imines and Nitriles

作者：Zhu, Baofu; Li, Wen; Chen, Haixin; Wu, Minjian; Hu, Jijing; Cao, Hua; Liu, Xiang^*

来源：Advanced Synthesis and Catalysis, 2022, 364(17): 2911-2915.

DOI：10.1002/adsc.202200463

• mechanochemical
• [3+2] cycloaddition
• azinium-N-imines
• nitriles
• 1,2,4-triazoles

We report here a mechanochemical Cu-catalyzed [3 + 2] cycloaddition of azinium-N-imines with nitriles under solventless grinding conditions. Various 1,2,4-triazolos derivatives were obtained in 51-80% yields. The developed protocol offers advantages in functional-group compatibility, scalability, no use of solvents, shorter reaction time, and without external heating. In addition, heterocyclic N-imines such as quinolinium and isoquinolinium salts are also suitable substrates, resulting in the production of 1,2,4-triazolo[1,5-a]quinoline and 1,2,4-triazolo [5, 1-a]isoquinoline derivatives under mechanochemical conditions.

• 单位
  广东药学院