Synthesis of multiple quinoline derivatives using novel ionic liquid-based nano-magnetic catalyst (MNPs@SiO2-Pr-AP-tribromide)

Abstract

Recently, magnetic iron oxide nanoparticles functionalized with various organic groups increasing attention in the synthesis of the organic compounds. In this study, ionic liquid nano-magnetic pyridinium-tribromide (MNPs@SiO 2 -Pr-AP-tribromide) as a new nano-catalyst was synthesized. The structure of the catalyst was identified by FT-IR, TGA, XRD, FE-SEM, EDX, EDS, TEM and VSM analysis. The nanocatalyst was efficient for the synthesis of quinoline derivatives through the one-pot reaction of 2-amino-5-chlorobenzophenone and pentane-2,4-dione. The advantages of this catalyst are easy preparation, large surface area, renewability, high thermal stability, high activity, shortening reaction time, improving efficiency, easy purification, and mild reaction conditions.

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

“…Kharazmi and co-workers synthesised quinoline derivatives 72 using IL-based nano-magnetic catalysts (MNPs@SiO 2 -Pr-AP-tribromide) via condensation of 2-amino aryl ketones 70 with methylene ketones 71 (Scheme 19 ) 73 in ethanol in 77–95% yields. After applying 3-chloropropyltriethoxysilane, 4-aminopyridine was grafted onto the silica-coated Fe 3 O 4 MNPs, and salt formation using HBr and Br 2 was then carried out.…”

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

“…Scheme 39 Catalytic transformation of glucose (66) into 121 using Brønsted-Lewis acidic tetraimidazolyl ILs Longo and co-workers have reported 1-(butyl-4-sulfonic)-3-methylimidazolium [(SO 3 H) 4 C 4 C 1 Im][OTf] ILs for the catalysis of Groebke-Blackburn-Bienayme reactions during the synthesis of imidazo[1,2-a]pyridines 125 using substituted aminopyridines 122, tert-butyl isocyanide (123) and substituted aldehydes 124 (Scheme 40). 101 The reaction in a sealed tube in ethanol/methanol under microwave irradiation was performed for 1-4 hours at 150 °C.…”

“…[115][116][117][118][119][120][121][122] Scheme 52 Synthesis of dihydropyrimidines 156 mediated by a pyridinium-based IL Ghorbani-Vaghei and colleagues conducted a synthesis of quinoline derivatives 159 by using a combination of 2aminobenzophenones 157 and methylene ketones 158 under reflux conditions in ethanol (Scheme 53). 123 They employed a nanomagnetic IL catalyst, namely MNPs@SiO 2 -Pr-AP-tribromide (100 mg), that was prepared by functionalizing silica-coated MNPs with 3-chloropropyltriethoxysilane, followed by loading 4-aminopyridine and salt formation using HBr/Br 2 . Importantly, the catalyst demonstrated reusability for up to six catalytic runs without a decrease in the yield of the final products 159.…”

“…ILs for the catalysis of Groebke-Blackburn-Bienayme reaction in synthesis of imidazo[1,2-a]pyridines (125) using substituted aminopyridine (122), tert-butyl isocyanide (123) and substituted aldehydes (124, Scheme 40). 100 The reaction in a sealed tube in ethanol/methanol under microwave irradiation was performed for 1-4 h at 150 o C. The key ILs were prepared using 1-methylimidazole and 1,4-butanesultone yielding zwitterions, which was further reacted with different acids.…”