Synthesis of fused 3-trifluoromethyl-1,2,4-triazoles via base-promoted [3+2] cycloaddition of nitrile imines and 1H-benzo[d]imidazole-2-thiols

Here we report a strategy for the facile assembly of fused 3-trifluoromethyl-1,2,4-triazoles, which are difficult to synthesize using traditional strategies, in 50-96% yields through a triethylamine-promoted intermolecular [3 + 2] cycloaddition pathway. This protocol features high efficiency, good functional group tolerance, mild conditions, and easy operation. Furthermore, a gram-scale reaction and product derivatizations were carried out smoothly to illustrate the practicability of this method.

Automated summary

This article presents a facile strategy for synthesizing fused 3-trifluoromethyl-1,2,4-triazoles, which are difficult to obtain using traditional methods. The strategy involves a triethylamine-promoted intermolecular [3 + 2] cycloaddition, with yields ranging from 50% to 96%. The method is highly efficient, tolerant towards various functional groups, conducted under mild conditions, and easy to execute. Furthermore, the scalability of the reaction and the ability to derivatize the product were demonstrated to highlight the practicality of this approach.