Hybrid nanoarchitectonics of cellulose-PMAA/layered double hydroxide: A novel reusable catalyst for the unsymmetrical Hantzsch reaction

Neochoritis, 2020, Multicomponent Reactions: “Kinderleicht, J. Chem. Educ., 97, 3739, 10.1021/acs.jchemed.0c00290 Preeti, 2021, Metal-free multicomponent reactions: a benign access to monocyclic six-membered N-heterocycles, Org. Biomol. Chem., 19, 2622, 10.1039/D1OB00145K Feng, 2021, Dimensional reduction of Lewis acidic metal-organic frameworks for multicomponent reactions, J. Am. Chem. Soc., 143, 8184, 10.1021/jacs.1c03561 Krishna, 2022, Synthesis of dihydropyrimidinones via multicomponent reaction route over acid functionalized metal-organic framework catalysts, J. Colloid Interface Sci., 607, 729, 10.1016/j.jcis.2021.09.031 do Nascimento, 2020, Niobium oxides as heterogeneous catalysts for Biginelli multicomponent reaction, J. Org. Chem., 85, 11170, 10.1021/acs.joc.0c01167 Qiao, 2021, Based on MFe2O4 NPs catalyzed multicomponent reactions: Green and efficient strategy in synthesis of heterocycles, Synth. Commun., 51, 2873, 10.1080/00397911.2021.1957112 Hadebe, 2022, A sustainable molybdenum oxide loaded on zirconia (MoO3/ZrO2) catalysed multicomponent reaction to synthesis novel dihydropyridines, Sustain. Chem. Pharm., 25 Noppawan, 2021, Vegetable oil as a highly effective 100% bio-based alternative solvent for the one-pot multicomponent Biginelli reaction, Green Chem, 23, 5766, 10.1039/D1GC00872B Zhang, 2022, An iron-catalyzed multicomponent reaction of cycloketone oxime esters, alkenes, DABCO-(SO2)2 and trimethylsilyl azide, Org. Chem. Front., 9, 917, 10.1039/D1QO01842F Brandao, 2021, The application of isatin-based multicomponent-reactions in the quest for new bioactive and drug-like molecules, Eur. J. Med. Chem., 211, 10.1016/j.ejmech.2020.113102 Rathee, 2020, Calcined layered double hydroxides: catalysts for xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivative synthesis, ACS Omega, 5, 15673, 10.1021/acsomega.0c01901 Quinonero, 2021, On the enantioselective phosphoric-acid-catalyzed Hantzsch synthesis of polyhydroquinolines, Org. Lett., 23, 3394, 10.1021/acs.orglett.1c00866 Parhad, 2022, Gallium Oxide (Ga2O3): An efficient heterogeneous nanocatalyst for one pot, multi-component synthesis of polyhydroquinolines, Polycycl. Aromat. Compd., 10.1080/10406638.2021.1957950 Aher, 2020, Quaternary vanado-molybdotungstophosphoric acid [H5PW6Mo4V2O40] over natural montmorillonite as a heterogeneous catalyst for the synthesis 4H-pyran and polyhydroquinoline derivatives, ChemistrySelect, 5, 7320, 10.1002/slct.202001065 Zare, 2020, Magnetic chitosan supported covalent organic framework/copper nanocomposite as an efficient and recoverable catalyst for the unsymmetrical hantzsch reaction, J. Taiwan. Inst. Chem. Eng., 116, 205, 10.1016/j.jtice.2020.10.028 Asadian, 2019, The first pyrazolium-based ionic liquid containing phosphotungstic acid immobilized on CuFe2O4@SiO2: A Recyclable organic-inorganic nanohybrid catalyst for the synthesis of polyhydroquinolines, Iran. J. Chem. Chem. Eng., 38, 65 Ramish, 2022, Microporous hierarchically Zn-MOF as an efficient catalyst for the Hantzsch synthesis of polyhydroquinolines, Sci. Rep., 12, 1479, 10.1038/s41598-022-05411-8 Karade, 2007, L-Proline as an efficient organo-catalyst for the synthesis of polyhydroquinoline via multicomponent Hantzsch reaction, Lett. Org. Chem., 4, 16, 10.2174/157017807780037405 Evans, 2009, Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines, Org. Lett., 11, 2957, 10.1021/ol901114f Behbahani, 2012, Synthesis of polyhydroquinoline derivatives through the Hantzsch four component using iron (III) phosphate as a catalyst, Synth React Inorg Met.-Org. Nano-Met. Chem., 42, 291, 10.1080/15533174.2011.610020 Surasani, 2012, FeF3 as a novel catalyst for the synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction, J. Fluor. Chem., 135, 91, 10.1016/j.jfluchem.2011.09.005 Adude, 2012, 3-Nitrophenylboronic acid-catalyzed efficient one-pot synthesis of 1,4-dihydropyridines and polyhydroquinolines, Int. J. Ind. Chem., 3, 1, 10.1186/2228-5547-3-6 Yoo, 2015, Bismuth(III) bromide catalyzed synthesis of polyhydroquinoline derivatives via the Hantzsch reaction, Tetrahedron Lett, 56, 4060, 10.1016/j.tetlet.2015.04.121 Jadhvar, 2017, One-pot synthesis and evaluation of anticancer activity of polyhydroquinoline derivatives catalyzed by [Msim]Cl, Res. Chem. Intermed., 43, 7211, 10.1007/s11164-017-3069-2 Somwanshi, 2017, LaCl3.7H2O: An efficient catalyst for one-pot multi-component Synthesis of 1,4-polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction, Iran. Chem. Commun., 5, 293 Friend, 2017, Heterogeneous catalysis: A central science for a sustainable future, Acc. Chem. Res., 50, 517, 10.1021/acs.accounts.6b00510 Kaneda, 2019, Design of high-performance heterogeneous catalysts using hydrotalcite for selective organic transformations, Green Chem, 21, 1361, 10.1039/C8GC03391A Chatterjee, 2021, The design and synthesis of heterogeneous catalysts for environmental applications, Dalton Trans, 50, 4765, 10.1039/D1DT00544H Zhang, 2021, Recent advances in heterogeneous catalysis for the nonoxidative conversion of methane, Chem. Sci., 12, 12529, 10.1039/D1SC02105B Xiong, 2020, In situ tuning of electronic structure of catalysts using controllable hydrogen spillover for enhanced selectivity, Nat. Commun., 11, 4773, 10.1038/s41467-020-18567-6 Vazhayil, 2021, Layered double hydroxide nanoclusters: aqueous, concentrated, stable, and catalytically active colloids toward green chemistry, Appl. Surf. Sci. Adv., 6 Mishra, 2018, Layered double hydroxides: A brief review from fundamentals to application as evolving biomaterials, Appl. Clay Sci., 153, 172, 10.1016/j.clay.2017.12.021 Rathee, 2020, Calcined layered double hydroxides: catalysts for xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivative synthesis, ACS Omega, 5, 15673, 10.1021/acsomega.0c01901 Kim, 2022, Simultaneous removal of cesium and iodate using prussian blue functionalized CoCr layered double hydroxide (PB-LDH), J. Environ. Chem. Eng., 10, 10.1016/j.jece.2022.107477 Murai, 2020, Layered double hydroxide nanosheets on plasmonic arrays of Al nanocylinders for optical sensing, ACS Appl. Nano Mater., 3, 5838, 10.1021/acsanm.0c01001 Shang, 2021, NO2 removal by adsorption on transition-metal-based layered double hydroxides, ACS ES&T Eng, 1, 375, 10.1021/acsestengg.0c00121 Mavric, 2021, Advances and challenges in industrial-scale water oxidation on layered double hydroxides, ACS Appl. Energy Mater., 4, 12032, 10.1021/acsaem.1c02604 Yang, 2021, Perspectives on multifunctional catalysts derived from layered double hydroxides toward upgrading reactions of biomass resources, ACS Catal, 11, 6440, 10.1021/acscatal.1c00699 Fagiolari, 2020, Iridium-doped nanosized Zn-Al layered double hydroxides as efficient water oxidation catalysts, ACS Appl. Mater. Interfaces, 12, 32736, 10.1021/acsami.0c07925 Hu, 2022, Hierarchical nickle-iron layered double hydroxide composite electrocatalyst for efficient oxygen evolution reaction, Mater. Today Nano, 17 K. Shanmuganathan, C.J. Ellison, Polymer green flame retardants, Chapter 20 - Layered double hydroxides: an emerging class of flame retardants, (2014) 675-707. Guo, 2010, Layered double hydroxide films: synthesis, properties and applications, Chem. Commun., 46, 5197, 10.1039/c0cc00313a Lin, 2022, Layered double hydroxides as reusable catalysts for cyclocondensation of amidines and aminoalcohols: access to multi-functionalized oxazolines, J. Org. Chem., 87, 1366, 10.1021/acs.joc.1c02696 Wang, 2021, A superior catalyst for ozone decomposition: NiFe layered double hydroxide, J. Environ. Sci., 10.1016/j.jes.2021.12.016 Gorlova, 2022, Synthesis, modification and application of layered double hydroxides as catalysts for Baeyer-Villiger oxidation, Catal. Today, 390-391, 69, 10.1016/j.cattod.2021.11.045 Xie, 2021, Synthesis, application and catalytic performance of layered double hydroxide based catalysts in advanced oxidation processes for wastewater decontamination: a review, Chem. Eng. Sci., 414, 10.1016/j.cej.2021.128713 Zhou, 2021, Efficient oxidation of biomass derived 5-hydroxymethylfurfural into 2,5-diformylfuran catalyzed by NiMn layered double hydroxide, Catal. Commun., 151, 10.1016/j.catcom.2021.106279 Sabzi, 2018, Characterization of bioactivity behavior and corrosion responses of hydroxyapatite-ZnO nanostructured coating deposited on NiTi shape memory alloy, Ceramics International, 44, 21395, 10.1016/j.ceramint.2018.08.197 S. Mersagh Dezfuli, M. Sabzi, Deposition of ceramic nanocomposite coatings by electroplating process: a review of layer-deposition mechanisms and effective parameters on the formation of the coating, 45 (2019) 21835-21842. Boroujerdnia, 2021, Synthesis and characterisation of a novel Fe-based nanocomposite by mechanical alloying and spark plasma sintering, Powder Metallurgy, 64, 283, 10.1080/00325899.2021.1904582 Sharma, 2021, Synthesis of MCM-41 supported cobalt (II) complex for the formation of polyhydroquinoline derivatives, Polyhedron, 199, 10.1016/j.poly.2021.115102 Rostamnia, 2014, Basic isoreticular metal-organic framework (IRMOF-3) porous nanomaterial as a suitable and green catalyst for selective unsymmetrical Hantzsch coupling reaction, Appl. Organomet. Chem., 28, 359, 10.1002/aoc.3136 Rathod, 2021, An eco-friendly synthesis of polyhydroquinoline derivatives using MoO3 promoted CeO2-ZrO2 solid heterogeneous catalyst, Mater. Today: Proc., 47, 1736 Nikoorazm, 2019, Core-shell nanostructure (Fe3O4@MCM-41@Cu-P2C) as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides, Chem. Phys. Lett., 737, 10.1016/j.cplett.2019.136784 Zhang, 2017, Covalently anchored tertiary amine functionalized ionic liquid on silica coated nano-Fe3O4 as a novel, efficient and magnetically recoverable catalyst for the unsymmetrical Hantzsch reaction and Knoevenagel condensation, RSC Adv, 7, 53861, 10.1039/C7RA10692K