Synthesis of fused 3-trifluoromethyl-1,2,4-triazoles <i>via</i> base-promoted [3 + 2] cycloaddition of nitrile imines and 1<i>H</i>-benzo[<i>d</i>]imidazole-2-thiols
Kaili Cen, Jiahao Wei, Yuting Feng, Yuan Liu, Xinye Wang, Yangyu Liu, Yalin Yin, Junhong Yu, Dahan Wang, Jinhui Cai
Abstract
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.
Topics & Concepts
ChemistryTriethylamineCycloadditionNitrileTrifluoromethylImidazoleIntermolecular forceCombinatorial chemistryFunctional groupBase (topology)Medicinal chemistryOrganic chemistryAlkylCatalysisMoleculePolymerMathematicsMathematical analysisFluorine in Organic ChemistryCyclopropane Reaction MechanismsClick Chemistry and Applications