Novel eco-friendly acacia gum-grafted-polyamidoxime@copper ferrite nanocatalyst for synthesis of pyrazolopyridine derivatives
Abstract
Abstract
A novel environmentally friendly polymer-based catalytic system was fabricated for the synthesis of biologically active pyrazolopyridine derivatives. Nanocatalyst was fabricated in three-step including (I) synthesis of the copper ferrite magnetic nanoparticles (MNPs) via co-precipitation method, (II) graft copolymerization of acrylonitrile onto acacia gum (AG) backbone using ammonium persulfate (APS) as an initiator, and
N, N'
-methylene bisacrylamide (MBA) as a crosslinker in combination with as-prepared copper ferrite, and (III) modification reaction of the as-prepared hydrogel using hydroxylamine hydrochloride reagent to achieve acacia gum-
grafted
- polyamidoxime/CuFe
2
O
4
(AG-
g-
PAO/CuFe
2
O
4
) hydrogel nanocatalyst. The fabricated hydrogel nanocatalyst was well characterized by different techniques. The results revealed that the fabricated hydrogel nanocatalyst exhibited high thermal stability with ~ 40% char yield at 800 °C. The existence of many acidic and basic sites such as hydroxyl, carboxylic acid, amidoxime, amide, as well as Cu
2+
in three-dimensional cross-linked structure caused it was showed a great catalytic performance in the pyrazolopyridine derivatives synthesis. The various corresponding products were synthesized in remarkable yields (90–97%) without difficult work-up procedure in short reaction times (15–40 min). Furthermore, the hydrogel catalyst showed superparamagnetic behavior, so it could be magnetically collected from the reaction mixture and recycled for at least five successive cycles without considerable loss of activity.
Graphical abstract
Keywords
- Acacia gum,
- Polyamidoxime,
- Graft copolymerization,
- Eco-friendly hydrogel catalyst,
- Pyrazolopyridine
References
- Wu and Chen (2012) Spontaneous synthesis of gold nanoparticles on gum arabic-modified iron oxide nanoparticles as a magnetically recoverable nanocatalyst 7(1) (pp. 1-7) https://doi.org/10.1186/1556-276X-7-317
- Khalil and Al-Matar (2013) Chitosan based heterogeneous catalyses: Chitosan-grafted-poly (4-vinylpyridne) as an efficient catalyst for michael additions and alkylpyridazinyl carbonitrile oxidation 18(5) (pp. 5288-5305) https://doi.org/10.3390/molecules18055288
- Baran et al. (2018) A new air and moisture stable robust bio-polymer based palladium catalyst for highly efficient synthesis of biaryl compounds 32(2) https://doi.org/10.1002/aoc.4076
- Kandathil et al. (2021) A green and sustainable cellulosic-carbon-shielded Pd–MNP hybrid material for catalysis and energy storage applications (pp. 395-407) https://doi.org/10.1007/s40097-020-00375-5
- Kumari et al. (2020) Cu (II) Schiff base complex grafted guar gum: Catalyst for benzophenone derivatives synthesis https://doi.org/10.1016/j.apcata.2020.117529
- Maleki et al. (2020) Magnetic dextrin nanobiomaterial: an organic-inorganic hybrid catalyst for the synthesis of biologically active polyhydroquinoline derivatives by asymmetric Hantzsch reaction https://doi.org/10.1016/j.msec.2019.110502
- Maleki et al. (2019) Preparation and characterization of an eco-friendly ZnFe2O4@ alginic acid nanocomposite catalyst and its application in the synthesis of 2-amino-3-cyano-4H-pyran derivatives (pp. 193-202) https://doi.org/10.1016/j.poly.2019.07.016
- Kamalzare et al. (2021) Chitosan magnetic nanocomposite: a magnetically reusable nanocatalyst for green synthesis of Hantzsch 1,4-dihydropyridines under solvent-free conditions 11(2) (pp. 229-243) https://doi.org/10.1007/s40097-020-00361-x
- Dohendou et al. (2021) Progresses in chitin, chitosan, starch, cellulose, pectin, alginate, gelatin and gum based (nano) catalysts for the Heck coupling reactions: A review (pp. 771-819) https://doi.org/10.1016/j.ijbiomac.2021.09.162
- Wang et al. (2021) Electrocatalytic nitrate/nitrite reduction to ammonia synthesis using metal nanocatalysts and bio-inspired metalloenzymes https://doi.org/10.1016/j.nanoen.2021.106088
- Han et al. (2014) One-step hydrothermal synthesis of 2D hexagonal nanoplates of α-Fe2O3/graphene composites with enhanced photocatalytic activity 24(36) (pp. 5719-5727) https://doi.org/10.1002/adfm.201401279
- Zheng et al. (2016) Hierarchical MoS2 nanosheet@ TiO2 nanotube array composites with enhanced photocatalytic and photocurrent performances 12(11) (pp. 1527-1536) https://doi.org/10.1002/smll.201503441
- Liu et al. (2016) Novel composites of α-Fe2O3 tetrakaidecahedron and graphene oxide as an effective photoelectrode with enhanced photocurrent performances 26(19) (pp. 3331-3339) https://doi.org/10.1002/adfm.201505554
- Hassanzadeh-Afruzi and Maleki (2022) Physical aspects of micro and nanoscale composites (pp. 69-86) Elsevier https://doi.org/10.1016/B978-0-12-824527-9.00012-5
- Hassanzadeh-Afruzi and Maleki (2022) Chemistry of micro and nanoscale composites (pp. 53-68) Elsevier https://doi.org/10.1016/B978-0-12-824527-9.00016-2
- Rahmati et al. (2021) Cu–curcumin/MCM-41 as an efficient catalyst for in situ conversion of carbazole to fuel oxygenates: a DOE approach https://doi.org/10.1007/s40097-021-00417-6
- Luo et al. (2021) Bio-conditioning poly-dihydromyricetin zinc nanoparticles synthesis for advanced catalytic degradation and microbial inhibition https://doi.org/10.1007/s40097-021-00443-4
- Mutlu et al. (2021) Green synthesis of Fe (II, III) oxides nanoparticles in the subcritical water medium and evaluation of their catalytic performance in the oxidation of metoprolol https://doi.org/10.1007/s40097-021-00403-y
- Feng and Dong (2007) Synthesis and characterization of phthaloyl-chitosan-g-poly (L-lactide) using an organic catalyst 70(3) (pp. 258-264) https://doi.org/10.1016/j.carbpol.2007.04.004
- El Assimi et al. (2019) Synthesis of poly (ε-caprolactone)-grafted guar gum by surface-initiated ring-opening polymerization (pp. 95-102) https://doi.org/10.1016/j.carbpol.2019.05.049
- Manawi et al. (2018) Enhancing lead removal from water by complex-assisted filtration with acacia gum (pp. 828-836) https://doi.org/10.1016/j.cej.2018.07.087
- Abdel-Bary and Elbedwehy (2018) Graft copolymerization of polyacrylic acid onto Acacia gum using erythrosine–thiourea as a visible light photoinitiator: Application for dye removal 75(8) (pp. 3325-3340) https://doi.org/10.1007/s00289-017-2205-x
- Priya et al. (2020) Fabricating a g-C3N4/CuO heterostructure with improved catalytic activity on the multicomponent synthesis of pyrimidoindazoles 10(4) (pp. 289-308) https://doi.org/10.1007/s40097-020-00350-0
- Bahrami et al. (2020) Synthesis and characterization of a novel and green rod-like magnetic ZnS/CuFe2O4/agar organometallic hybrid catalyst for the synthesis of biologically-active 2-amino-tetrahydro-4H-chromene-3-carbonitrile derivatives 34(11) https://doi.org/10.1002/aoc.5949
- Hassanzadeh-Afruzi et al. (2021) Magnetized melamine‐modified polyacrylonitrile (PAN@ melamine/Fe3O4) organometallic nanomaterial: Preparation, characterization, and application as a multifunctional catalyst in the synthesis of bioactive dihydropyrano [2, 3‐c] pyrazole and 2‐amino‐3‐cyano 4H‐pyran derivatives 35(10) https://doi.org/10.1002/aoc.6363
- Azizi et al. (2020) Iron oxide magnetic nanoparticles supported on amino propyl-functionalized KCC-1 as robust recyclable catalyst for one pot and green synthesis of tetrahydrodipyrazolopyridines and cytotoxicity evaluation 34(3) https://doi.org/10.1002/aoc.5440
- Manjunatha et al. (2017) A Cryptosporidium PI (4) K inhibitor is a drug candidate for cryptosporidiosis 546(7658) (pp. 376-380) https://doi.org/10.1038/nature22337
- Salem and Ali (2016) Novel pyrazolo [3, 4-b] pyridine derivatives: synthesis, characterization, antimicrobial and antiproliferative profile 39(4) (pp. 473-483) https://doi.org/10.1248/bpb.b15-00586
- Sindhu et al. (2016) Synthesis and biological evaluation of some functionalized 1 H-1, 2, 3-triazole tethered pyrazolo [3, 4-b] pyridin-6 (7 H)-ones as antimicrobial and apoptosis inducing agents 25(9) (pp. 1813-1830) https://doi.org/10.1007/s00044-016-1604-0
- Maqbool et al. (2014) Pyrazolopyridines II: synthesis and antibacterial screening of 6-aryl-3-methyl-1-phenyl-1H-pyrazolo [3, 4-b] pyridine-4-carboxylic Acids 26(10) (pp. 2870-2872) https://doi.org/10.14233/ajchem.2014.15918
- Gudmundsson et al. (2008) Pyrazolopyridines with potent activity against herpesviruses: Effects of C5 substituents on antiviral activity 18(3) (pp. 1157-1161) https://doi.org/10.1016/j.bmcl.2007.11.120
- Quiroga et al. (2017) Synthesis and antifungal in vitro evaluation of pyrazolo [3, 4-b] pyridines derivatives obtained by Aza-Diels–Alder reaction and microwave irradiation 65(2) (pp. 143-150) https://doi.org/10.1248/cpb.c16-00652
- Chioua et al. (2009) Synthesis and biological evaluation of 3, 6-diamino-1H-pyrazolo [3, 4-b] pyridine derivatives as protein kinase inhibitors 19(16) (pp. 4566-4569) https://doi.org/10.1016/j.bmcl.2009.06.099
- Hajizadeh et al. (2020) "Cu (ii) immobilized on Fe 3 O 4@ HNTs–tetrazole (CFHT) nanocomposite: synthesis, characterization, investigation of its catalytic role for the 1, 3 dipolar cycloaddition reaction, and antibacterial activity 10(44) (pp. 26467-26478) https://doi.org/10.1039/D0RA04772D
- Tao et al. (2000) Preparation and gas-sensing properties of CuFe2O4 at reduced temperature (pp. 172-176) https://doi.org/10.1016/S0921-5107(00)00473-6
- Zohuriaan-Mehr et al. (2005) New super-absorbing hydrogel hybrids from gum arabic and acrylic monomers 42(12) (pp. 1655-1666) https://doi.org/10.1080/10601320500246859
- Juby et al. (2012) Silver nanoparticle-loaded PVA/gum acacia hydrogel: Synthesis, characterization and antibacterial study 89(3) (pp. 906-913) https://doi.org/10.1016/j.carbpol.2012.04.033
- Alang et al. (2011) Synthesis and optimization of polyacrylamide and gum arabic graft copolymer 5(4) (pp. 1694-1702)
- Zonatto et al. (2017) Adsorption and controlled release of potassium, phosphate and ammonia from modified Arabic gum-based hydrogel (pp. 363-369) https://doi.org/10.1016/j.ijbiomac.2017.07.051
- de Souza et al. (2019) Paulino, Arabic gum-based composite hydrogels reinforced with eucalyptus and pinus residues for controlled phosphorus release (pp. 33-42) https://doi.org/10.1016/j.ijbiomac.2019.08.106
- Surendra et al. (2018) Green and chemical-engineered CuFe 2 O 4: characterization, cyclic voltammetry, photocatalytic and photoluminescent investigation for multifunctional applications 8(1) (pp. 45-59) https://doi.org/10.1007/s40097-018-0253-x
- Elbedwehy et al. (2019) Super effective removal of toxic metals water pollutants using multi functionalized polyacrylonitrile and arabic gum grafts 11(12) https://doi.org/10.3390/polym11121938
- Rezaei et al. (2018) Low temperature CO oxidation over mesoporous iron and copper mixed oxides nanopowders synthesized by a simple one-pot solid-state method (pp. 379-388) https://doi.org/10.1016/j.psep.2018.08.024
- Rajput et al. (2015) CuFe2O4 magnetic heterogeneous nanocatalyst: Low power sonochemical-coprecipitation preparation and applications in synthesis of 4H-chromene-3-carbonitrile scaffolds (pp. 229-240) https://doi.org/10.1016/j.ultsonch.2015.01.008
- Iqbal et al. (2011) A study of the influence of crystallite size on the electrical and magnetic properties of CuFe2O4 46(11) (pp. 1837-1842) https://doi.org/10.1016/j.materresbull.2011.07.036
- Agouriane et al. (2016) Structural and magnetic properties of CuFe2O4 ferrite nanoparticles synthesized by co-precipitation 7(11) (pp. 4116-4120)
- Rahman et al. (2020) Poly (amidoxime) ligand derived from waste palm fiber for the removal of heavy metals from electroplating wastewater 27(27) (pp. 34541-34556) https://doi.org/10.1007/s11356-020-09462-0
- Li et al. (2019) symbiotic aerogel fibers made via in-situ gelation of aramid nanofibers with polyamidoxime for uranium extraction 24(9) https://doi.org/10.3390/molecules24091821
- Hindi et al. (2017) Synthesis, characterization and biodegradation of gum Arabic-based bioplastic membranes 4(2) (pp. 32-42)
- Emam (2019) Arabic gum as bio-synthesizer for Ag–Au bimetallic nanocomposite using seed-mediated growth technique and its biological efficacy 27(1) (pp. 210-223) https://doi.org/10.1007/s10924-018-1331-3
- Nilmoung et al. (2016) Electrospun carbon/CuFe2O4 composite nanofibers with improved electrochemical energy storage performanceJ (pp. 1131-1140) https://doi.org/10.1016/j.jallcom.2016.06.251
- Maleki et al. (2019) Mesoporous halloysite nanotubes modified by CuFe 2 O4 spinel ferrite nanoparticles and study of its application as a novel and efficient heterogeneous catalyst in the synthesis of pyrazolopyridine derivatives 9(1) (pp. 1-8) https://doi.org/10.1038/s41598-019-42126-9
- Safaei-Ghomi et al. (2016) A pseudo six-component process for the synthesis of tetrahydrodipyrazolo pyridines using an ionic liquid immobilized on a FeNi 3 nanocatalyst 6(40) (pp. 33676-33685) https://doi.org/10.1039/C6RA02906J
- Dashteh et al. (2021) Novel pseudopolymeric magnetic nanoparticles as a hydrogen bond catalyst for the synthesis of tetrahydrodipyrazolopyridine derivatives under mild reaction conditions 35(6) https://doi.org/10.1002/aoc.6222
- Verma et al. (2020) Tetrahydropyrazolopyridines as antifriction and antiwear agents: experimental and DFT calculations 10(17) (pp. 10188-10196) https://doi.org/10.1039/D0RA00794C
- Chinthaparthi et al. (2021) Green synthesis and anticancer activity of tetrahydrodipyrazolo [3, 4-b: 4′, 3′-e] pyridines catalyzed by phospho sulfonic acid 58(5) (pp. 1104-1116) https://doi.org/10.1002/jhet.4241
- Tamaddon and Arab (2019) Urease covalently immobilized on cotton-derived nanocellulose-dialdehyde for urea detection and urea-based multicomponent synthesis of tetrahydro-pyrazolopyridines in water 9(71) (pp. 41893-41902) https://doi.org/10.1039/C9RA05240B
- Shahbazi-Alavi et al. (2016) Nano-CuCr2O4: an efficient catalyst for a one-pot synthesis of tetrahydrodipyrazolopyridine 40(6) (pp. 361-363) https://doi.org/10.3184/174751916X14628044763653
- Safaei-Ghomi et al. (2016) Synthesis of pyrazolopyridines catalyzed by nano-CdZr 4 (PO 4) 6 as a reusable catalyst 42(12) (pp. 8143-8156)
- Salehi and Mirjalili (2018) Nano-ovalbumin: a green biocatalyst for biomimetic synthesis of tetrahydrodipyrazolo pyridines in water 44(11) (pp. 7065-7077) https://doi.org/10.1007/s11164-018-3542-6
10.1007/s40097-022-00471-8