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

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 1H NMR, 13C NMR, 19F 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-diaryl-decahydroacridines 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.

我们合成了一种新型离子液体（ionic liquid）{N,N,N',N'-四甲基乙二胺-N,N'-二磺酸三氟乙酸盐([TMEDSA][TFA]₂)}，并通过¹H核磁共振（¹H NMR）、¹³C核磁共振（¹³C NMR）、¹⁹F核磁共振（¹⁹F NMR）、质谱、热重分析（TG, thermogravimetry）以及差示扫描量热法（DSC, differential scanning calorimetry）对其结构进行了表征。随后，我们将[TMEDSA][TFA]₂作为双功能催化剂，用于通过5,5-二甲基-1,3-环己二酮（dimedone）与芳醛、伯胺的多组分反应制备1,8-二氧代-9,10-二芳基十氢吖啶类化合物。此外，我们基于该催化剂的双功能特性，提出了一种合理且极具吸引力的反应机理。由于[TMEDSA][TFA]₂兼具酸性与碱性位点，且两类位点各有两个，因此该催化剂具有极高的催化活性与普适性，可高产率得到目标产物。