Cu2+-encapsulated ZIF-8 as a facile catalyst for the synthesis of kojic acid derivatives in aqueous medium: A green approach

Results in Chemistry - Tập 4 - Trang 100604 - 2022
S. Tirumala Santosh Kumar1, Saratchandra Babu Mukkamala1, P. Atchutha Rao1, Nandigama Satish Kumar1,2
1Nanoscience and Nanotechnology Laboratory, Department of Chemistry, Gitam Institute of Science, GITAM, Vishakapatnam, India
2Department of Chemistry, Rajiv Gandhi University of Knowledge Technologies, Srikakulam, India

Tài liệu tham khảo

Bentley, 2006, From miso, sake and shoyu to cosmetics: a century of science for kojic acid, R, Nat. Prod. Rep., 23, 1046, 10.1039/b603758p Brtko, 2004, Kojic Acid and Its Derivatives: History and Present State Of Art, Cent. Eur. J. Publ. Health, 12, 16 Burdock, 2001, Evaluation of Health Aspects of Kojic Acid in Food, Regul. Toxicol. Pharmacol., 33, 80, 10.1006/rtph.2000.1442 Maeda, 1991, In vitro effectiveness of several whitening cosmetic components in human melanocytes, J. Soc. Cosmet. Chem., 42, 361 Yamamoto, 1987, Synthesis and Antitumor Activity of Tropolone Derivatives. 6.' Structure-Activity Relationships of Antitumor-Active Tropolone and 8-Hydroxyquinoline Derivatives, J. Med. Chem., 30, 1897, 10.1021/jm00393a035 Jennings, 1945, Nature (London)., 155, 302, 10.1038/155302a0 Reddy, 2010, Indium(III) chloride catalyzed three-component coupling reaction: A novel synthesis of 2-substituted aryl(indolyl)kojic acid derivatives as potent antifungal and antibacterial agents, Bioorg. Med. Chem. Lett., 24, 7507, 10.1016/j.bmcl.2010.10.003 Sco, 2000, Cu2+-doped zeolitic imidazolate frameworks (ZIF-8): Efficient and stable catalysts for cycloadditions and condensation reactions, Nature., 404, 982 Hayshi, 2007, Zeolite A imidazolate frameworks, Nat. Mater., 6, 501, 10.1038/nmat1927 Thallapally, 2008, Flexible (Breathing) Interpenetrated Metal-Organic Frameworks for CO2 Separation Applications, J. Am. Chem. Soc., 130, 16842, 10.1021/ja806391k Britt, 2008, Metal-organic frameworks with high capacity and selectivity for harmful gases, Proc. Natl. Acad. Sci. U. S. A., 105, 11623, 10.1073/pnas.0804900105 Li, 2009, Selective gas adsorption and separation in metal–organic frameworks, Chem. Soc. Rev., 38, 1477, 10.1039/b802426j Xiang, 2010, Multiscale simulation and modelling of adsorptive processes for energy gas storage and carbon dioxide capture in porous coordination frameworks, Energy Environ. Sci., 3, 1469, 10.1039/c0ee00049c Benmansour, 2010, Polynitrile anions as ligands: From magnetic polymeric architectures to spin crossover materials, Chem. Rev., 254, 1468 Morris, 2008, Gas Storage in Nanoporous Materials, Angew. Chem., Int. Ed., 47, 4966, 10.1002/anie.200703934 Farha, 2010, De novo synthesis of a metal–organic framework material featuring ultrahigh surface area and gas storage capacities, Nat. Chem., 2, 944, 10.1038/nchem.834 Chen, 2006, A Microporous Metal–Organic Framework for Gas-Chromatographic Separation of Alkanes, Angew. Chem, Int. Ed., 45, 1390, 10.1002/anie.200502844 Lee, 2009, Metal–organic framework materials as catalysts, Chem. Soc. Rev., 38, 1450, 10.1039/b807080f Liédana, 2012, Coronas, CAF@ZIF-8: One-Step Encapsulation of Caffeine in MOF, ACS Appl. Mater. Interfaces., 4, 5016, 10.1021/am301365h Mahmoodi, 2019, Environmentally friendly ultrasound-assisted synthesis of magnetic zeolitic imidazolate framework - Graphene oxide nanocomposites and pollutant removal from water, J. Mol. Liq., 282, 115, 10.1016/j.molliq.2019.02.139 Furukawa, 2013, The Chemistry and Applications of Metal-Organic Frameworks, Science, 341, 10.1126/science.1230444 Liu, 2014, Applications of metal–organic frameworks in heterogeneous supramolecular catalysis, Chem. Soc. Rev., 43, 6011, 10.1039/C4CS00094C Yap, 2017, Synthesis and applications of MOF - derived porous nanostructures, Green, Energy Environ., 2, 218 Tran, 2011, Expanding Applications of Metal-Organic Frameworks: Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction, ACS Catal., 1, 120, 10.1021/cs1000625 Jin, 2013, ZIF-8 crystal coatings on a polyimide substrate and their catalytic behaviours for the Knoevenagel reaction, Dalton Trans., 42, 3936, 10.1039/c2dt32161k Zanon, 2017, Zn@ZIF-67 as Catalysts for the Knoevenagel Condensation of Aldehyde Derivatives with Malononitrile, CatalLett., 147, 2410 Yang, 2014, Zeolitic imidazole framework-67 as an efficient heterogeneous catalyst for the synthesis of ethyl methyl carbonate, Catal. Commun., 54, 86, 10.1016/j.catcom.2014.05.021 Amarante, 2017, Evaluation of basic sites of ZIFs metal organic frameworks in the Knoevenagel condensation reaction, Appl. Catal. A., 548, 47, 10.1016/j.apcata.2017.08.006 Asefi, 2010, Effect of nonionic co-surfactants on corrosion inhibition effect of cationic Gemini surfactant, Colloids and Surfaces A: Physicochem, Eng. Aspects., 355, 183, 10.1016/j.colsurfa.2009.12.019 Asefi, 2009, The chain length influence of cationic surfactant and role of nonionic co-surfactants on controlling the corrosion rate of steel in acidic media, Corrosion Science., 51, 1817, 10.1016/j.corsci.2009.05.007 Azad, 2019, Appl. Organometal Chem., 33, 4952, 10.1002/aoc.4952 Schejn, 2015, Cu2+-doped zeolitic imidazolate frameworks (ZIF-8): Efficient and stable catalysts for cycloadditions and condensation reactions, Catal. Sci. Technol., 5, 1829, 10.1039/C4CY01505C Davies, 2016, On the Role of Water in Heterogeneous Catalysis: A Tribute to Professor M. Wyn Roberts, Top. Catal., 59, 671, 10.1007/s11244-016-0539-5 Hayati, 2015, Dendrimer–Titania nanocomposite: synthesis and dye-removal capacity, Res. Chem. Intermed., 41, 3743, 10.1007/s11164-013-1486-4 Almasian, 2015, Preparation and Adsorption Behavior of Diethylenetriamine/Polyacrylonitrile Composite Nanofibers for a Direct Dye Removal, Fibers Polym., 16, 1925, 10.1007/s12221-015-4624-3 F. Hosseini, S. Sadighian, H. Hosseini-Monfared, N. M. Mahmoodi, Dye removal and kinetics of adsorption by magnetic chitosan nanoparticles, 57, (2016), 24378-24386. doi:10.1080/19443994.2016.1143879. Wang, 2012, organocatalytic enantioselective Michael addition of a kojic acid derivative to nitro olefins, Org. Biomol. Chem., 10, 2950, 10.1039/c2ob07192d Reddy, 2014, Enantioselective 1,4-addition of kojic acid derivatives to b-nitroolefins catalyzed by a cinchonine derived sugar thiourea, RSC Adv., 4, 9107, 10.1039/c3ra47423b Kataev, 2016, Supramolecular catalysis by b-cyclodextrin for the synthesis of kojic acid derivatives in water, New J. Chem., 40, 1693, 10.1039/C5NJ01902H Kumar, 2015, Catalyst-Free, One-Pot, Three-Component Approach for the Synthesis of 2-[1-Aryl-2-(azaaryl)ethyl]malononitriles via sp3 C–H Activation of 2-Methyl Azaarenes, Synlett, 26, 1808, 10.1055/s-0034-1380212 Kumar, 2017, Acid-Catalyzed Protocol for the Synthesis of Novel 6-Substituted Tetrahydroquinolines by Highly Regioselective C6-Functionalization of Tetrahydroquinolines with Chromene Hemiacetals or β-Nitrostyrenes, Synthesis, 49, 3171, 10.1055/s-0036-1588995 Kumar, 2018, An Efficient and Environmentally Benign Protocol for the 1,6-Michael Addition of Nitroalkanes to 3-Methyl-4-nitro-5-styrylisoxazoles in WERSA, ChemistrySelect., 3, 1915, 10.1002/slct.201702788 Ramesh, 2019, Cu doped ZIF Catalyzed Synthesis of Propargyl Amines with Quaternary Carbon Center Under Solvent Free Conditions, ChemistrySelect., 3, 9045, 10.1002/slct.201901729