Nanomagnetic NH₂·MIL-101(Fe)/ED as a new highly efficient catalyst for the synthesis of thiopyran and oxospiro-indolinethiopyran derivatives

References

• Hasani M, Kalhor HR. Enzyme-inspired lysine-modified carbon quantum dots performing carbonylation using urea and a cascade reaction for synthesizing 2-benzoxazolinone. ACS Catal. 2021;11:10778–10788.
   Web of Science ®Google Scholar
• Abedi M, Hosseini M, Arabmarkadeh A, et al. Magnetic nanocatalysts in A3-coupling reactions. Synth Commun. 2021;51:835–855.
   Web of Science ®Google Scholar
• Gupta S. Sulfuric acid heterogenized on magnetic nanoparticles functionalized with glycerol catalyzed synthesis of 2, 3-dihydroquinazoline-4 (1H)-ones. J Synth Chem. 2022; 1:37–41.
   Google Scholar
• Kazemi M, Ghobadi M, Mirzaie A. Cobalt ferrite nanoparticles (CoFe2O4 MNPs) as catalyst and support: magnetically recoverable nanocatalysts in organic synthesis. Nanotechnol Rev. 2018;7:43–68.
   Web of Science ®Google Scholar
• Moghaddam FM, Jarahiyan A, Haris MH, et al. High catalytic performance of CoCuFe2O4/ZIF-8 (Zn) nanocatalyst for synthesis of new benzimidazole derivatives. J Mol Struct. 2023;1285:135496.
   Web of Science ®Google Scholar
• Kazemi M. Based on magnetic nanoparticles: gold reusable nanomagnetic catalysts in organic synthesis. Synth Commun. 2020;50(14):2079–2094.
   Web of Science ®Google Scholar
• Kazemi M, Shiri L. Ionic liquid immobilized on magnetic nanoparticles: a nice and efficient catalytic strategy in synthesis of heterocycles. J Synth Chem. 2022;1:1–7.
   Google Scholar
• Wang H, Bao Z, Wu H, et al. Two solvent-induced porous hydrogen-bonded organic frameworks: solvent effects on structures and functionalities. ChemComm. 2017;53:11150–11153.
   PubMed Web of Science ®Google Scholar
• Bhosle SD, Jadhav KA, Itage SV, et al. Zn catalyzed a simple and convenient method for thiourea synthesis. J Sulfur Chem. 2023;44:186–200.
   Web of Science ®Google Scholar
• Moghaddam FM, Eslami M, Aghamiri B. A diastereo and chemo selective synthesis of 6-amino-4-aryl-3-oxo-2, 3, 3a, 4-tetrahydro-1H-pyrazolo [3, 4-b] pyridine-5-carbonitrile under environmentally benevolent conditions. J Mol Struct 2022;1257:132601.
   Web of Science ®Google Scholar
• Li F, Sun L, Teng Y, et al. Highly diastereo-and enantioselective organocatalytic one-pot sequential 1, 4-addition/dearomative-fluorination transformation. Chem Eur J 2012;18:14255–14260.
   PubMed Web of Science ®Google Scholar
• Aubin LB, Wagner TM, Thoburn JD, et al. Dynamic NMR studies of a potential chiroptical switch based on dithiocarbamate–iminodithiolane interconversion. Org Lett. 2001;3:3413–3416.
   PubMed Web of Science ®Google Scholar
• Dong ZB, Liu X, Bolm C. Copper-catalyzed C (sp2)–S coupling reactions for the synthesis of aryl dithiocarbamates with thiuram disulfide reagents. Org Lett. 2017;19:5916–5919.
   PubMedGoogle Scholar
• Mazzarella D, Magagnano G, Schweitzer-Chaput B, et al. Photochemical organocatalytic borylation of alkyl chlorides, bromides, and sulfonates. ACS Catal. 2019;9:5876–5880.
   Web of Science ®Google Scholar
• Moghaddam FM, Aghamiri B, Jalalinik M. A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions. Synth Commun. 2022;52:175–184.
   Web of Science ®Google Scholar
• Moghaddam FM, Saberi V, Karimi A. Highly diastereoselective cascade [5 + 1] double Michael reaction, a route for the synthesis of spiro (thio) oxindoles. Sci Rep. 2021;11:1–11.
   PubMed Web of Science ®Google Scholar
• Moghaddam FM, Goudarzi M, Chamani F, et al. A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds. New J Chem. 2020;44:9699–9702.
   Web of Science ®Google Scholar
• Dodd LJ, Omar O, Wu X, et al. Investigating the role and scope of catalysts in inverse vulcanization. ACS Catal. 2021;11:4441–4455.
   Web of Science ®Google Scholar
• Zhang Z, Nie X, Wang F, et al. Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic polymers. Nat Commun. 2020;11:1–10.
   PubMed Web of Science ®Google Scholar
• Mizojiri R, Takami K, Ito T, et al. Efficient and stereoselective syntheses of isomerically pure 4-aminotetrahydro-2 H-thiopyran 1-oxide derivatives. Org Process Res Dev. 2017;21:1034–1041.
   Web of Science ®Google Scholar
• Ali TE, Assiri MA. A convenient one-pot synthesis of novel functionalized thiophene,: thieno [2, 3-b] thiophene, thiopyran, and thiopyrano [2, 3-b] thiopyran bearing phosphonate groups. J Sulfur Chem 2021;42:490–498.
   Web of Science ®Google Scholar
• Corbet M, de Greef M, Zard SZ. A highly conjunctive β-keto phosphonate: application to the synthesis of pyridine alkaloids Xestamines C, E, and H. Org Lett 2008;10:253–256.
   PubMed Web of Science ®Google Scholar
• Bodaghifard MA, Mobinikhaledi A, Asadbegi S. Bis (4-pyridylamino) triazine-stabilized magnetite nanoparticles: preparation,: characterization and application as a retrievable catalyst for the green synthesis of 4H-pyran, 4H-thiopyran and 1, 4-dihydropyridine derivatives. Appl Organomet Chem. 2017;31:e3557.
   Web of Science ®Google Scholar
• Kaur N. Synthesis of six-membered N-heterocycles using ruthenium catalysts. Catal Lett. 2019;149:1513–1559.
   Web of Science ®Google Scholar
• Li J, Liu J, Liu S, et al. Uranyl-MOF for thioether oxidation processes under visible light conditions. Catal Lett. 2021;151:2982–2989.
   Web of Science ®Google Scholar
• Dubey R, Singh VK, Sharma LK, et al. A convenient electro-catalyzed multicomponent synthesis of 4 H-thiopyran derivatives. New J Chem. 2017;41:7836–7839.
   Web of Science ®Google Scholar
• Bio MM, Hansen KB, Gipson JA. Practical, efficient synthesis of 1, 1-dioxo-hexahydro-1λ6-thiopyran-4-carbaldehyde. Org Process Res Dev 2008;12:892–895.
   Web of Science ®Google Scholar
• Brayshaw SK, Clarke LP, Homanen P, et al. Coordination behavior and transformations of thienyl-substituted diacetylenes upon coordination to Os3H2 (CO) 10. Organometallics. 2011;30:3955–3965.
   Web of Science ®Google Scholar
• Hutchinson JH, Charleson S, Evans JF, et al. Thiopyranol [2, 3, 4-c, d] indoles as inhibitors of 5-lipoxygenase, 5-lipoxygenase-activating protein, and leukotriene C4 synthase. J Med Chem 1995;38:4538–4547.
   PubMed Web of Science ®Google Scholar
• Hepworth JD, Heron BM. Thiopyrans and their benzo derivatives. Chem Heterocycl Compounds. 2008;7:727–954.
   Google Scholar
• Pinate P, Makone S. Novel DABCO based acidic ionic liquid as a green protocol for the synthesis of thiazolidin-4-one derivatives and cytotoxic activity evaluation on human breast cancer cell line. J Sulfur Chem 2023;44:20–36.
   Web of Science ®Google Scholar
• Pasha GF, Asghari S, Tajbakhsh M, et al. Synthesis and characterization of sulfide, sulfoxide and sulfone derivatives of thiopyran: antimicrobial evaluation. Res Chem Intermed. 2017;43:7291–7306.
   Web of Science ®Google Scholar
• Verma RK, Verma GK, Shukla G, et al. 4-Dimethylamino pyridine-promoted one-pot three-component regioselective synthesis of highly functionalized 4 H-thiopyrans via heteroannulation of β-oxodithioesters. ACS Comb Sci. 2012;14:224–230.
   PubMed Web of Science ®Google Scholar
• Abdel-Latif FF. Heterocycles synthesis through reactions of indolin-2-one derivatives with active methylene and amino reagents: part 3, novel and facile one-step synthesis of spirothiopyran-4-yl indolidene derivatives. Phosphorus Sulfur Silicon Relat Elem. 1990;53:145–148.
   Web of Science ®Google Scholar
• Moghaddam FM, Aghamiri B. Facile one-pot, multi-component reaction to synthesize spirooxindole-annulated thiopyran derivatives under environmentally benevolent conditions. Heliyon. 2022;8:e10666.
   PubMed Web of Science ®Google Scholar
• Liu W, Chen S, Zhang F, et al. Design, synthesis and biological evaluation of novel antitumor spirodihydrothiopyran-oxindole derivatives. Bioorganic Med Chem Lett. 2019;29:1636–1642.
   PubMedGoogle Scholar
• Moghaddam FM, Pourkaveh R. Nano cobalt ferrite catalyzed coupling reaction of nitroarene and alkyl halide: An odorless and ligand-free rout to unsymmetrical thioether synthesis. Catal Commun. 2017;94:33–37.
   Web of Science ®Google Scholar
• Xiong P, Zhang H, Li G, et al. Adsorption removal of ibuprofen and naproxen from aqueous solution with Cu-doped Mil-101 (Fe). Sci Total Environ. 2021;797:149179.
   PubMed Web of Science ®Google Scholar
• Hwang YK, Hong DY, Chang JS, et al. Amine grafting on coordinatively unsaturated metal centers of MOFs: consequences for catalysis and metal encapsulation. Angew Chem. 2008;120:4212–4216.
   Google Scholar
• Liu R, Chi L, Wang X, et al. Effective and selective adsorption of phosphate from aqueous solution via trivalent-metals-based amino-MIL-101 MOFs. Chem Eng J. 2019;357:159–168.
   Web of Science ®Google Scholar
• Kandiah M, Usseglio S, Svelle S, et al. Post-synthetic modification of the metal–organic framework compound UiO-66. J Mater Chem. 2010;20:9848–9851.
   Web of Science ®Google Scholar
• Chenampulli S, Unnikrishnan G, Thomas S, et al. Novel ethylene diamine functionalised nanocellulose/poly (ethylene-co-acrylic acid) composites for biomedical applications. Cellulose. 2019;26:1795–1809.
   Web of Science ®Google Scholar
• Farisabadi A, Moradi M, Hajati S, et al. Controlled thermolysis of MIL-101 (Fe, Cr) for synthesis of FexOy/porous carbon as negative electrode and Cr2O3/porous carbon as positive electrode of supercapacitor. Appl Surf Sci 2019;469:192–203.
   Web of Science ®Google Scholar
• Doan VD, Huynh BA, Le Pham HA, et al. Cu2O/Fe3O4/MIL-101 (Fe) nanocomposite as a highly efficient and recyclable visible-light-driven catalyst for degradation of ciprofloxacin. Environ Res. 2021;201:111593.
   PubMed Web of Science ®Google Scholar
• Zhao S, Ma D, Jin W. Preparation of CoFe2O 4 nanocrystallites by solvothermal process and its catalytic activity on the thermal decomposition of ammonium perchlorate. J Nanomater. 2010;2010:1–5.
   Web of Science ®Google Scholar
• He L, Dong Y, Zheng Y, et al. A novel magnetic MIL-101 (Fe)/TiO2 composite for photo degradation of tetracycline under solar light. J. Hazard. Mater. 2019;361:85–94.
   PubMed Web of Science ®Google Scholar