2025/07/09 by Kohzadian, Alireza, Filian, Hossein, Fathollahi, Rohollah
#Aldehydes #Green solvent #Ionic liquid #N #N'-alkylidene bisamides
paper · doi:10.57647/j.ijc.2025.1503.31
In the current study, a new Brønsted-acidic ionic liquid, namely trimethyl-tris(4-pyridinium)benzene trifluoroacetate ([TMPB][TFA]), was synthesized as a high-performance, reproducible acidic-basic catalyst. The structure of the ionic liquid was characterized by various physicochemical techniques. In continuation, the catalytic effect of [TMPB][TFA] in the production of N, N'-alkylidene bisamides was monitored via a one-pot pseudo three-component condensation of a wide range of aldehydes with benzamide/acetamide. The enhancement of this synthetic pathway was carried out using 10 mol% ionic liquid in ethanol solvent at 60°C. The important features of this process include: the dual function of IL as an acid-base duel in the activation of reactants, comprehensiveness of the protocol in the rapid production of a variety of derivatives in high yields (1a-17a, 85 to 98%, 9 to 30 min), the ability to recover and reuse the IL for up to three cycles while maintaining catalytic efficiency, moderate reaction conditions, easy work-up, producing and characterizing new compounds (8a and 9a), and green reaction environment without using expensive metal precursors, harsh temperature conditions as well as non-benign solvents. Highlights • Synthesis and characterization of a novel ionic liquid based on the trifluoroacetate anion. • Fast and facile synthesis of N,N'-alkylidene bisamides. • Ability to use ionic liquid up to three runs without significant reduction in catalytic activity. • Represents advantages: the dual function of IL as an acid-base duel in the activation of reactants, generality, short reaction times, high yields of the products, simple work-up, and good compliance with green chemistry protocols.