Design, preparation and characterization of a new ionic liquid, 1,3-disulfonic acid benzimidazolium chloride, as an efficient and recyclable catalyst for the synthesis of tetrahydropyridine under solvent-free conditions

Abstract

In the present work, 1,3-disulfonic acid benzimidazolium chloride as a new ionic liquid, is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR as well as mass spectra.

Kinetic study on alkylation of hydroquinone with methanol over SO3H functionalized Brønsted acidic ionic liquids

“…Asymmetric and symmetric stretching frequencies of the sulphonic acid and hydrogen sulphate 580, 1054 574, 1030 Abbasi [29] C-H wagging vibrations of imidazolium ring 758 749 Rathika and Suthanthiraraj [30] Symmetric N-S stretching vibration 877 872 Dutta et al [31] O-SO 2 symmetric and asymmetric stretching 1170, 1311 1148, 1309 Shirini et al [32] C=N stretching, C-C aromatic stretching 1500-1700 1500-1700 Rathika and Suthanthiraraj [30] OH of the SO 3 H groups, C-H stretching of imidazolium and benzene ring 2800-3200 2800-3200 Moosavi-Zare et al [33] intermediate I4, which further reacts with methanol to form intermediate I6. Here, the reaction pathway follows the Michael addition mechanism.…”

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

“…Abbasi synthesized a new ionic liquid 1,3‐disulfonic acid benzimidazolium chloride ([Dsbim]Cl). Using a catalytic, amount of this ionic liquid as catalyst, a series of functionalized piperidines was prepared starting from two equivalents of aromatic aldehydes, two equivalents of anilines and one equivalent ethyl acetoacetate under solvent‐free conditions at 80 °C (Scheme ).…”

“…Ionic liquid 1-methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO 4 ]) efficiently catalyzed the one-pot pseudo fivecomponent reactions of various aromatic aldehydes, anilines and β-ketoesters to afford the corresponding highly substituted functionalized piperidines in ethanol under reflux condition (Scheme 51). [88] Abbasi [89] synthesized a new ionic liquid 1,3-disulfonic acid benzimidazolium chloride ([Dsbim]Cl). Using a catalytic, amount of this ionic liquid as catalyst, a series of functionalized piperidines was prepared starting from two equivalents of aromatic aldehydes, two equivalents of anilines and one equivalent ethyl acetoacetate under solvent-free conditions at 80°C (Scheme 52).…”

Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids

“…Starting from the first report by Katritzky et al [45], BILs were investigated in fields that comprise CO 2 capture and conversion [46,47], electronics [48][49][50], dye solar cells [51], anticancer and antibacterial agents [52,53], bioremediation technologies [54,55], fuel desulfurization [56], extraction [57], lignin conversion [58], and fuel cell [59,60]. On the other hand, an area in which BILs were heavily studied is organic synthesis, where they were successfully used as catalysts in several reaction classes such as the Biginelli reaction [61], the Micheal reaction [62,63], condensations [64][65][66][67], alkylations [68], amine formylation [69], coupling [70], and esterifications [71]. Furthermore, the use of BILs as catalysts has also been reported in the preparation of natural-derived building blocks: in the transesterification of castor oil with methanol [72], in the production of ethyl levulinate [73] and in the preparation of 5-hydroxymethyl furfural starting from chitosan [74].…”