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Preparation and Characterization of Hollow MgO/SiO2 Nanocomposites and Using as Reusable Catalyst for Synthesis of 1 H-isochromenes

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Abstract

In the present study, a hollow MgO/SiO2 nanocatalyst with high alkaline properties was prepared. This heterogeneous catalyst was prepared in several steps to create a great active area and decrease the density of the catalyst. The alkaline hollow catalyst framework was applied for the reaction of cyclohexanone, malononitrile and benzaldehyde for synthesis of 1 H-isocromene therough the Michael addition and aldol condensation reaction at room temperature. In this method, all of the done reactions were excellent in the yields of products and reaction times. At the end of the reaction, the nanocatalyst separated by simple filtration and reuse in several runs elsewhere.

Graphic Abstract

In the present study, hollow MgO/SiO2 nanocatalyst with great base properties was made. Thisheterogeneous catalyst was a synthesis in several steps to create a great active area and decreasethe density of the catalyst

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Data Availability

Electronicsupplementary material contains 1 H NMR, 13 C NMR, FT-IR and microscopy data.

References

  1. Butin AV, Abaev VT, Mel’chin VV, Dmitriev AS (2005) Furan ring opening-isochromene ring closure: A new approach to isochromene ring synthesis. Tetrahedron Lett 46:8439–8441. https://doi.org/10.1016/j.tetlet.2005.09.056

    Article  CAS  Google Scholar 

  2. Hasan SA, Elias AN, Farhan MS (2015) Synthesis, characterization and antimicrobial evaluation of a series of chalcone derivatives. Der Pharma Chem 7:39–42. https://doi.org/10.1002/jhet

    Article  CAS  Google Scholar 

  3. Singh IP, Bodiwala HS (2010) Recent advances in anti-HIV natural products. Nat Prod Rep 27:1781–1800. https://doi.org/10.1039/C0NP00025F

    Article  CAS  PubMed  Google Scholar 

  4. Tomás-Mendivil E, Starck J, Ortuno JC, Michelet V (2015) Synthesis of functionalized 1H-isochromene derivatives via a Au-catalyzed domino cycloisomerization/reduction approach. Org Lett 17:6126–6129. https://doi.org/10.1021/acs.orglett.5b03146

    Article  CAS  PubMed  Google Scholar 

  5. Mondal S, Nogami T, Asao N, Yamamoto Y (2003) Synthesis of novel antitumor agent benzo [ g ] isochromene carboxylic acid (3-Dimethylylaminopropyl) amide with a dual role Pd ( II ) Catalyst enhancing the electrophilicity of the alkyne bond, for 9496–9498. https://doi.org/10.1021/JO035016X

  6. Morimoto K, Hirano K, Satoh T, Miura M (2011) Synthesis of isochromene and related derivatives by rhodium-catalyzed oxidative coupling of benzyl and allyl alcohols with alkynes. J Org Chem 76:9548–9551. https://doi.org/10.1021/jo201923d

    Article  CAS  PubMed  Google Scholar 

  7. Shishido Y, Wakabayashi H, Koike H, Ueno N, Nukui S, Yamagishi T, Murata Y, Naganeo F, Mizutani M, Shimada K, Fujiwara Y, Sakakibara A, Suga O, Kusano R, Ueda S, Kanai Y, Tsuchiya M, Satake K (2008) Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’  Bioorg Med Chem 16:7193–7205. https://doi.org/10.1016/j.bmc.2008.06.047

    Article  CAS  PubMed  Google Scholar 

  8. Wang W, Li T, Milburn R, Yates J, Hinnant E, Luzzio MJ, Noble SA, Attardo G (1998) Novel 1,3-disubstituted-5,10-dihydro-5,10-dioxo-1H-mbenzo[g]isochromene-3-carboxamides as potent antitumor agents. Bioorg Med Chem Lett 8:1579–1584. https://doi.org/10.1016/S0960-894X(98)00274-1

    Article  CAS  PubMed  Google Scholar 

  9. Papadakis DP, Salemik CA, Alikaridis FJ, Kephalas TA (1983) Isolation and identification of new cannabinoids in cannabis smoke. Tetrahedron 39:2223–2225. https://doi.org/10.1016/S0040-4020(01)91942-8

    Article  CAS  Google Scholar 

  10. Wang D, Liu S, Lan XC, Paniagua A, Hao WJ, Li G, Tu SJ, Jiang B (2017) Tunable dimerization and trimerization of β-Alkynyl Ketones via silver catalysis for accessing spiro and dispiro compounds containing 1H-Isochromene. Adv Synth Catal 359:3186–3193. https://doi.org/10.1002/adsc.201700543

    Article  CAS  Google Scholar 

  11. Verin SV, Kuznetsov EV, Revinskii YV, Yufit DS, Struchkov YT (1991) A novel dimerization reaction of 1-Methyl-2-benzopyrylium salts. Mendeleev Commun 1:104–106. https://doi.org/10.1070/MC1991v001n03ABEH000064

    Article  Google Scholar 

  12. Budov VV (1994) Hollow glass microspheres. use, properties, and technology (Review). Glas Ceram 51:230–235. https://doi.org/10.1007/BF00680655

    Article  Google Scholar 

  13. Cao C-Y, Cui Z-M, Chen C-Q, Song W-G, Cai W (2010) Ceria hollow nanospheres produced by a template-free microwave-assisted hydrothermal method for heavy metal ion removal and catalysis. J Phys Chem C 114:9865–9870. https://doi.org/10.1021/jp101553x

    Article  CAS  Google Scholar 

  14. Chen J-F, Ding H-M, Wang J-X, Shao L (2004) Preparation and characterization of porous hollow silica nanoparticles for drug delivery application. Biomaterials 25:723–727. https://doi.org/10.1016/S0142-9612(03)00566-0

  15. Fang B, Kim JH, Kim M-S, Bonakdarpour A, Lam A, Wilkinson DP, Yu J-S (2012) Fabrication of hollow core carbon spheres with hierarchical nanoarchitecture for ultrahigh electrical charge storage. J Mater Chem 22:19031–19038. https://doi.org/10.1039/C2JM33435F

  16. Ikeda S, Tachi K, Ng YH, Ikoma Y, Sakata T, Mori H, Harada T, Matsumura M (2007) Selective adsorption of glucose-derived carbon precursor on amino-functionalized porous silica for fabrication of hollow carbon spheres with porous walls. Chem Mater 19:4335–4340. https://doi.org/10.1021/cm0702969

    Article  CAS  Google Scholar 

  17. Russell PSJ, Hölzer P, Chang W, Abdolvand A, Travers JC (2014) Hollow-core photonic crystal fibres for gas-based nonlinear optics. Nat Photonics 8:278

    Article  CAS  Google Scholar 

  18. Caruso RA, Susha A, Caruso F (2001) Multilayered titania, silica, and laponite nanoparticle coatings on polystyrene colloidal templates and resulting inorganic hollow spheres. Chem Mater 13:400–409. https://doi.org/10.1021/cm001175a

    Article  CAS  Google Scholar 

  19. Hentze H-P, Raghavan SR, McKelvey CA, Kaler EW (2003) Silica hollow spheres by templating of catanionic vesicles. Langmuir 19:1069–1074. https://doi.org/10.1021/la020727w

    Article  CAS  Google Scholar 

  20. Imhof A (2001) Preparation and characterization of titania-coated polystyrene spheres and hollow titania shells. Langmuir 17:3579–3585. https://doi.org/10.1021/la001604j

    Article  CAS  Google Scholar 

  21. Titirici M-M, Antonietti M, Thomas A (2006) A generalized synthesis of metal oxide hollow spheres using a hydrothermal approach. Chem Mater 18:3808–3812. https://doi.org/10.1021/cm052768u

    Article  CAS  Google Scholar 

  22. Wang Y, Su F, Lee JY, Zhao XS (2006) Crystalline carbon hollow spheres, crystalline carbon – SnO2 hollow spheres, and crystalline SnO2 hollow spheres: synthesis and performance in reversible Li-Ion storage. Chem Mater 18:1347–1353. https://doi.org/10.1021/cm052219o

    Article  CAS  Google Scholar 

  23. Lai X, Halpert JE, Wang D (2012) Recent advances in micro-/nano-structured hollow spheres for energy applications: From simple to complex systems. Energy Environ Sci 5:5604–5618. https://doi.org/10.1039/C1EE02426D

  24. Li L, Qing-Sheng W, Ya-Ping D, Pei-Ming W (2005) Control synthesis of semiconductor ZnSe quasi-nanospheres by reverse micelles soft template. Mater Lett 59:1623–1626. https://doi.org/10.1016/j.matlet.2004.06.077

  25. Liu J, Yang T, Wang D-W, Lu GQ, Max), Zhao D, Qiao SZ (2013) A facile soft-template synthesis of mesoporous polymeric and carbonaceous nanospheres. Nat Commun 4:2798

    Article  Google Scholar 

  26. Sasidharan M, Nakashima K (2014) Core–shell–corona polymeric micelles as a versatile template for synthesis of inorganic hollow nanospheres. Acc Chem Res 47:157–167. https://doi.org/10.1021/ar4001026

    Article  CAS  PubMed  Google Scholar 

  27. Wang Z, Chen M, Wu L (2008) Synthesis of monodisperse hollow silver spheres using phase-transformable emulsions as templates. Chem Mater 20:3251–3253. https://doi.org/10.1021/cm8001223

    Article  CAS  Google Scholar 

  28. Naeimi H, Mohammadi S (2020) Synthesis of 1H-isochromenes, 4H‐chromenes, and ortho‐aminocarbonitrile tetrahydronaphthalenes from the same reactants by using metal‐free catalyst. J Heterocycl Chem 57:50–59

  29. Fang X, Chen C, Liu Z, Liu P, Zheng N (2011) A cationic surfactant assisted selective etching strategy to hollow mesoporous silica spheres. Nanoscale 3:1632–1639. https://doi.org/10.1039/c0nr00893a

  30. Wang DP, Zeng HC (2009) Multifunctional roles of TiO2nanoparticles for architecture of complex core-shells and hollow spheres of SiO2– TiO2- polyaniline system. Chem Mater 21:4811–4823. https://doi.org/10.1021/cm901509t

  31. Naeimi H, Mohammadi S (2020) Synthesis of 1H-Isochromenes, 4H‐Chromenes and orthoaminocarbonitrile tetrahydronaphthalenes by CaMgFe2O4 Base Nanocatalyst. ChemistrySelect 5:2627–2633

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Acknowledgements

The authors are grateful to University of Kashan for supporting this work by Grant No. 159148/96.

Funding

See Acknowledgements above.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, 87317- 51167, Kashan, Iran

    Somaye Mohammadi & Hossein Naeimi

Authors
  1. Somaye Mohammadi
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  2. Hossein Naeimi
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Contributions

H. Naeimi and S. Mohammadi conceived and designed the experiments and also they contributed to the interpretation of the results. S. Mohammadi carried out the experiments and synthesis of products and also provided the primary draft of the manuscript. H. Naeimi supervised the project and revised the final version of the manuscript. All authors approved the final version of the manuscript to be published.

Corresponding author

Correspondence to Hossein Naeimi.

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Highlight

• The hollow MgO/SiO2 nanocatalyst was used as active base catalyst.

• The products were characterized using melting point, FT-IR and 1H NMR techniques.

• The products were obtained in excellent yields and short reaction times.

• The hollow MgO/SiO2 nanocatalyst as efficient catalyst was employed in synthesis of

1H-isocromenes.

Supplementary Information

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Mohammadi, S., Naeimi, H. Preparation and Characterization of Hollow MgO/SiO2 Nanocomposites and Using as Reusable Catalyst for Synthesis of 1 H-isochromenes. Silicon 14, 6881–6893 (2022). https://doi.org/10.1007/s12633-021-01378-9

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  • DOI: https://doi.org/10.1007/s12633-021-01378-9

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