Polymer Support Immobilized Acidic Ionic Liquid: Preparation and Its Application as Catalyst in the Synthesis of Hantzsch 1,4-Dihydropyridines

Abstract

A polymer support immobilized acidic ionic liquid was prepared by copolymerization of 3-vinyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate with styrene in the presence of benzoyl peroxide and its primary application as a solid acidic heterogeneous catalyst to the synthesis of Hantzsch 1,4-dihydropyridines through a one-pot three-component reaction of aromatic aldehydes, ethyl acetoacetate and ammonium acetate was investigated. The results showed that this heterogeneous catalyst has high catalytic activity and the desired products were obtained in good to high yields. Moreover, the catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.

(NH4)42[MoVI72MoV60O372(CH3COO)30(H2O)72] as a Heterogeneous Reusable Catalyst for Organic Reactions: Mini-Review

“…1,4-dihydropyridine plays significant roles in synthesis of valuable organic compounds that have various biological properties [70][71][72]. Many synthetic protocols were developed to accelerate the rate of 1,4-DHPs reaction and to improve the yield at the presence of various catalysts [73][74][75][76]. Despite all of these useful methods, further improvement of the synthesis process was essential.…”

Lewis acidic mesoporous Fe-TUD-1 as catalysts for synthesis of Hantzsch 1,4-dihydropyridine derivatives

“…is well-known [9]. Various catalysts such as ruthenium trichloride [10], Mg 3 N 2 [11], KHSO 4 [12], K 7 [PW 11 CoO 40 ] [13], ionic liquids based catalysts [14][15][16][17], microwave-assisted bismuth nitrate [18], p-toluenesulphonic acid [18], FeF 3 [19], non-ionic surfactant Triton X-100 [20], Zn-VCO 3 hydrotalcite [21], montmorillonite K10 [22], Fe nanoparticle [23], mesoporous alumina sulphuric acid [24], trifluoroethanol [25] and visible light [26,27] have been reported for the synthesis of DHP derivatives. Though some of these catalysts have their advantages, disadvantages include use of environmentally harmful and expensive reagents, large excess of catalyst, low yields, recovery and heterogeneity of the catalyst.…”

Acid-ionic polymer as recyclable catalyst for one-pot three-component Mannich reaction

“…17,18 Recently, BAILs has proven to be effective catalysts in the Mannich reactions. 18 Solid-supported acidic ionic liquid catalysts [19][20][21][22][23][24][25][26] have been reported for acetalization reaction, 20 condensation, 21 Hantzsch reaction, 22 multicomponent reaction, 23 esterication, 24 hydrolysis of cellulose 25 and biodiesel synthesis. 26 Herein, we would like to present the utilization of polystyrene bearing acidic ionic liquid (acid-IP) as a reusable heterogeneous catalyst for direct-Mannich reaction of aldehydes, amines and ketones in one-pot process under mild, convenient and metal-free conditions at ambient temperature (Scheme 1).…”