10.57647/j.ijc.2025.1503.31

Facile synthesis of N,N'-alkylidene bisamides catalyzed by trimethyl-tris(4-pyridinium)benzene trifluoroacetate: an efficient and rapid approach

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  • Alireza Kohzadian*1,
  • Hossein Filian1,
  • Rohollah Fathollahi1,
  1. Takin Shimi Sepanta Industries Co, Sirvan Industrial Zone, PO 6958140120, Ilam, Iran
Facile synthesis of N,N'-alkylidene bisamides catalyzed by trimethyl-tris(4-pyridinium)benzene trifluoroacetate: an efficient and rapid approach

Received: 2025-03-08

Revised: 2025-05-11

Accepted: 2025-06-06

Published in Issue 2025-07-01

Copyright (c) 2025 Alireza Kohzadian, Hossein Filian, Fathollahi (Author)

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This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

Kohzadian, A., Filian, H., & Fathollahi, R. (2025). Facile synthesis of N,N’-alkylidene bisamides catalyzed by trimethyl-tris(4-pyridinium)benzene trifluoroacetate: an efficient and rapid approach. Iranian Journal of Catalysis, 15(3 (September 2025). https://doi.org/10.57647/j.ijc.2025.1503.31
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Abstract

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.

 

Keywords

  • Ionic liquid,
  • Aldehydes,
  • Green solvent,
  • N,N'-­alkylidene bisamides
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