FSM-16-SO₃H nanoparticles as a novel heterogeneous catalyst: preparation, characterization, and catalytic application in the synthesis of polyhydroquinolines

Abstract

FSM-16-SO3H nanoparticles were prepared using a sol-gel method at room temperature. The prepared FSM-16-SO3H was used to catalyze the synthesis of polyhydroquinolines through a one-pot, four-component reaction of aldehydes, dimedone, ethyl cyanoacetate, and ammonium acetate under reflux condition in EtOH as a green solvent. To investigate the textural properties of the prepared catalyst, various techniques were applied such as X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscope, and Brunauer–Emmett–Teller. High catalytic activity, easy handling, and thermal stability are the superior properties that could be denoted after successive investigations of this catalyst. In addition, the catalyst can be recovered easily and reused effectively for several cycles.

Schiff Base Complex of Copper Immobilized on Core–Shell Magnetic Nanoparticles Catalyzed One-Pot Syntheses of Polyhydroquinoline Derivatives under Mild Conditions Supported by a DFT Study

“…The PHQ derivatives are prepared by a one-pot four-component Hantzsch reaction of aldehydes, 1,3-cyclohexanedione compounds, ammonium acetate, and ethyl acetoacetate. According to the importance of PHQ derivatives as a precursor to some important classes of drugs, a vast number of catalysts have been developed for the synthesis of the PHQ derivatives including the magnetic chitosan terephthaloyl-creatine bionanocomposite, SPIONs-Cr­(VI), Fe 3 O 4 /SiO 2 –OSO 3 H, biogenic gold nanoparticles (AuNPs), SBA-15@AMPD-Co, FeAl 2 O 4 MNPs, Hercynite@SiO 2 - l -arginine-Ni, FSM-16-SO 3 H, Sc­(OTf) 3 , [Fe 3 O 4 @SiO 2 @(CH 2 ) 3 Py]­HSO 4 – , CoFe 2 O 4 @Pr, Cu@SB-MCM-41, MCM-41, Cu­(II)-PAA/M-MCM-41 NC, L-HSO 4 @SBA-15, gadolinium triflate, MCM-41@PDCA-Co, magnetic dextrin, MoO 3 /CeO 2 –ZrO 2 , TrzMOP, and bismuth­(III) bromide . Unfortunately, some of the reported procedures have one or more drawbacks, such as harsh reaction conditions, tedious workup procedures, high loading catalyst, use of nonreusable catalyst, high temperature, use of toxic metals and volatile organic solvents, and need for prolonged reaction times.…”

Synthesis of hydrazone-based polyhydroquinoline derivatives – antibacterial activities, α-glucosidase inhibitory capability, and DFT study

“…10,11 Several methods have been reported for the synthesis of PHQ and its derivatives to enhance their yields. [12][13][14][15] The literature review indicates that in different synthetic methods, various kinds of catalysts are used in the synthesis of polyhydroquinolines, for instance, mesoporous vanadium ion-doped titania nanoparticles, 14 sulfonic acidfunctionalized SBA-15 (SBA-Pr-SO 3 H), 16 FSM-16-SO 3 H, cobalt(II) complex, 17 Fe 3 O 4 /SiO 2 -OSO 3 H nanostructure catalyst, 18 an acidic ionic liquid immobilized onto magnetic Fe 3 O 4 as an efficient heterogeneous catalyst, 19 L-proline, 20 Zn-MOF microspheres, 21 HY-zeolite, 22 HClO 4 -SiO 2 , 23 and chitosan-decorated copper nanoparticles. 24,25 However, these methods have some limitations, such as the requirement for expensive catalysts, toxicity of catalysts, harsh reaction conditions, and low product yields.…”

Solvent‐Free Hantzsch Condensation Reaction Leading to Polyhydroquinoline and 1,8‐Dioxo‐decahydroacridine Derivatives Promoted by Nanosized Kaolin‐[BTMSP]‐NH2+ HSO4−

“…However, this classic process suffers from several disadvantages, such as long reaction time, use of a large quantity of volatile organic solvents and low yield. [1,9] Since then, a large number of catalysts such as Fe 3 O 4 -adenine-Ni, [10] L-proline, [11,12] ED/MIL-101(Cr), [13] molecular iodine, [14] Yb-(OTf) 3 , [15] ceric Ammonium Nitrate, [16] K 7 [PW 11 CoO 40 ], [17] ZnO, [18] glycine, [19] PPA-SiO 2 , [20] FeF 3 , [21] Cd(NO 3 ) 2 .4H 2 O, [22] polyethylene glycol, [23] ChCl/urea, [24] nano-γ-Fe 2 O 3 -SO 3 H, [25] IRMOF-3, [4] Ga 2 O 3, [26] SBA-15@AMPDÀ Co, [27] nicotinic acid, [28] Nidithizone@boehmite, [29] TEDETA@BNPs, [30] ascorbic acid, [31] La 3 + / 4A, [32] Fe 3 O 4 @B-MCM-41, [33] and BiBr 3 [34] have been used to improve the Hantzsch reaction conditions. Although each of the reported catalysts and techniques has its advantages, nevertheless further efforts are needed to introduce more efficient and cleaner catalytic systems for the synthesis of the above mentioned important target molecules.…”

“…The preparation of 1,4‐DHPs was first reported by Arthur Hantzsch in 1882 through a one‐pot condensation of aldehydes, β ‐ketoesters, and ammonia in acetic acid or ethanol. However, this classic process suffers from several disadvantages, such as long reaction time, use of a large quantity of volatile organic solvents and low yield [1,9] . Since then, a large number of catalysts such as Fe 3 O 4 ‐adenine‐Ni, [10] L ‐proline, [11,12] ED/MIL‐101(Cr), [13] molecular iodine, [14] Yb(OTf) 3 , [15] ceric Ammonium Nitrate, [16] K 7 [PW 11 CoO 40 ], [17] ZnO, [18] glycine, [19] PPA‐SiO 2 , [20] FeF 3 , [21] Cd(NO 3 ) 2 .4H 2 O, [22] polyethylene glycol, [23] ChCl/urea, [24] nano‐γ‐Fe 2 O 3 ‐SO 3 H, [25] IRMOF‐3, [4] Ga 2 O 3, [26] SBA‐15@AMPD−Co, [27] nicotinic acid, [28] Ni‐dithizone@boehmite, [29] TEDETA@BNPs, [30] ascorbic acid, [31] La 3+/ 4A, [32] Fe 3 O 4 @B‐MCM‐41, [33] and BiBr 3 [34] have been used to improve the Hantzsch reaction conditions.…”