Production, Characterization and Usage of a Novel Disulfonic Acid-Functionalized Ionic Liquid as a Highly Efficient and Dual-Functional Catalyst for the Synthesis of 1,8-Dioxo-9,10-Diaryl-Decahydroacridines

Abstract

We have produced a novel ionic liquid {N,N,N',N'-tetramethylethylene-diaminium-N,N'-disulfonic acid trifluoroacetate ([TMEDSA] [TFA] 2)}, and identified it by analysis of 1 H NMR, 13 C NMR, 19 F NMR, mass, TG (thermogravimetry) and DSC (differential scanning calorimetry) data. Then, we have applied [TMEDSA][TFA] 2 as a dual-functional catalyst for the production of 1,8-dioxo-9,10-diaryldecahydroacridines by the multi-component reaction of dimedone with arylaldehydes and primary amines. Furthermore, we have proposed a plausible and attractive mechanism based on dual-functionality of the catalyst. Due to dual-functionality of [TMEDSA] [TFA] 2 (possessing acidic and basic sites), and also possessing two sites of each, it was highly effective and general, and produced the products in high yields.

N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

“…Although in our previous work we were able to regenerate similar catalysts as employed here [38], we believe that the preparation of them from fresh N,N,N′,N′tetramethylethylene-diamine or pyridine is more economic, greener and easier than their regeneration. [9,10]. All known compounds were identified by comparison of their melting points and/or spectral data with those reported in the literature.…”

“…Ionic liquids (ILs) have attracted great attention for their use as attractive reaction media, reagents and catalysts in organic synthesis. The inimitable properties of ILs, which caused their wide applications in this field, include thermal and chemical stability, non-volatility, non-flammability, broad temperature range of the liquid state, aptitude to solve a wide range of compound classes, appropriate electrochemical window, catalyzation of various organic transformations and their capability to be functionalized for different purposes [1][2][3][4][5][6][7][8][9][10]. Among the ILs, Brønsted acids have been particularly found to be effective catalysts in several organic syntheses [4][5][6][7][8][9][10].…”