Ionic Liquid Supported on Magnetic Graphene Oxide as a Highly Efficient and Stable Catalyst for the Synthesis of Triazolopyrimidines

Abstract

A novel sulfonic acid functionalized ionic liquid was prepared by anchoring 1-(propyl-3-sulfonate) vinylimidazolium hydrogen sulfate ([(CH2)3SO3HVIm]HSO4) on Fe3O4@GO. The prepared heterogeneous catalyst was characterized by XRD, FT-IR, EDX, SEM, VSM and TGA techniques. The results show that [(CH2)3SO3HVIm]HSO4 was successfully deposited on the surface of Fe3O4@GO and the prepared ionic liquid catalyst exhibited good thermal stability. The activity of the prepared catalyst was investigated in the synthesis of triazolo[1,5-a]pyrimidine derivatives by a one-pot three-component reaction of active methylene compound (malononitrile or ethyl cyanoacetate), 3-amine-1H-1,2,4-triazole and aryl aldehydes under solvent-free conditions. This catalyst could be rapidly separated by an external magnet and recycled seven times without significant loss of catalytic activity.

Ionic liquid immobilized on modified magnetic FSM-16: an efficient and magnetically recoverable nanocatalyst

“…2b). 54,56,57 As shown in Fig. 2c, the XRD pattern of Fe 3 O 4 @FSM-16 is in good agreement with the XRD pattern of previous reports of Fe 3 O 4 coated FSM-16 structures (Fe 3 O 4 @FSM-16).…”

“…1a, the absorption bands revealed at 574 and 3400 cm −1 are attributed to Fe–O and O–H bonds, respectively. 54,56 Also, in Fig. 1b, the peaks at 474, 806, and 1106 cm −1 correspond to asymmetric and symmetric stretching vibrations of the Si–O–Si group.…”

“…Polyhydroquinoline derivatives are usually synthesized via the four-compound one-pot reaction of aldehyde, dimedone, ethyl acetoacetate, ammonium acetate, and the corresponding catalyst. [49][50][51] In continuation of our studies program for the synthesis of novel heterogeneous nanocatalysts and also considering the importance of mesoporous materials in the catalysis synthesis process, 12,[52][53][54][55][56][57][58] herein, a recyclable magnetic catalyst based on FSM-16 (Fe 3 O 4 @FSM-16-SO 3 /IL) has been synthesized and characterized. Furthermore, Fe 3 O 4 @FSM-16-SO 3 /IL was used as an effective catalyst in the synthesis of polyhydroquinoline derivatives via the one-pot reaction of various aromatic aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate.…”

A novel ionic liquid immobilized on FSM-16: a novel recoverable nanocatalyst for the synthesis of biscoumarin derivatives

“…4,5 Despite these promising advantages, ionic liquids have suffered from some disadvantages that have prevented them from being widely used in practice, including high cost, intolerable viscosity, cumbersome product purification, and long reaction times. 6,7 Immobilization of ionic liquids on solid supports is one of the most efficient ways to overcome the above-mentioned drawbacks. 8,9 An exciting combining feature of ionic liquid with those of the supporting material will develop novel performances when synergistic effects appear.…”

A novel magnetic FSM-16 supported ionic liquid/Pd complex as a high performance and recyclable catalyst for the synthesis of pyrano[3,2-c]chromenes

“…[29][30][31] However, the utilization of these nanoparticles is hampered by their instability in acidic and alkaline environments, the tendency to aggregate and deform in some organic solvents, and easy oxidation. 32,33 Therefore, Fe 3 O 4 magnetic nanoparticles are coated with a range of materials, including mesoporous silica materials, [34][35][36] polymers, 37 carbon nanotubes, 38 cellulose, 39,40 graphene oxide, 41 biochar, 42 and boehmite nanoparticles, 43 resulting in the formation of core-shell structures. These coatings may enhance the stability, performance, and biocompatibility, making them suitable for various applications in nanocatalysts, biomedicine, and nanotechnology.…”