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. 2022 Apr 1;12(17):10219-10236.
doi: 10.1039/d2ra00212d. eCollection 2022 Mar 31.

Metal-bio functionalized bismuthmagnetite [Fe3- x Bi x O4/SiO2@l-ArgEt3 +I-/Zn(ii)]: a novel bionanocomposite for the synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[ b][1,4]diazepine malononitriles and malonamides at room temperature and under sonication

Fatemeh Molaei Yielzoleh  1 , Kobra Nikoofar  1
Affiliations

Metal-bio functionalized bismuthmagnetite [Fe3- x Bi x O4/SiO2@l-ArgEt3 +I-/Zn(ii)]: a novel bionanocomposite for the synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[ b][1,4]diazepine malononitriles and malonamides at room temperature and under sonication

Fatemeh Molaei Yielzoleh et al. RSC Adv. .

Abstract

In this work, a new magnetized composite of bismuth (Fe3-x Bi x O4) was prepared and functionalized stepwise with silica, triethylargininium iodide ionic liquid, and Zn(ii) to prepare a multi-layered core-shell bio-nanostructure, [Fe3-x Bi x O4/SiO2@l-ArgEt3 +I-/Zn(ii)]. The modified bismuth magnetic amino acid-containing nanocomposite was characterized using several techniques including Fourier-transform infrared (FT-IR), X-ray fluorescence (XRF), vibrating sample magnetometer (VSM), field-emission scanning electron microscopy (FESEM), energy dispersive X-ray analysis (EDAX), thermogravimetric/differential scanning calorimetric (TGA/DSC) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer-Emmett-Teller (BET), and inductively coupled plasma-optical emission spectrometry (ICP-OES). The magnetized bionanocomposite exhibited high catalytic activity for the synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine malononitriles via five-component reactions between 1,2-phenylenediamines, Meldrum's acid, malononitrile, aldehydes, and isocyanides at room temperature in ethanol. The efficacy of this protocol was also examined to obtain malonamide derivatives via pseudo six-component reactions of 1,4-phenylenediamine, Meldrum's acid, malononitrile, aldehydes, and isocyanides. When the above-mentioned MCRs were repeated under the same conditions with the application of sonication, a notable decrease in the reaction time was observed. The recovery and reusability of the metal-bio functionalized bismuthmagnetite were examined successfully in 3 runs. Furthermore, the characteristics of the recovered Fe3-x Bi x O4/SiO2@l-ArgEt3 +I-/Zn(ii) were investigated though FESEM and EDAX analysis.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii) bionanocomposite.
Scheme 2
Scheme 2. Synthesis of 4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine malononitriles 6a–g and malonamides 7a–f in the presence of nano Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Fig. 1
Fig. 1. FT-IR spectra of (a) Fe3−xBixO4, (b) Fe3−xBixO4/SiO2, (c) Fe3−xBixO4/SiO2@l-Arg, (d) Fe3−xBixO4/SiO2@l-ArgEt3+I−, and (e) Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Fig. 2
Fig. 2. EDAX analysis of Fe3−xBixO4 (top) and Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii) (bottom).
Fig. 3
Fig. 3. FESEM images of Fe3−xBixO4 (top) and Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii) (bottom).
Fig. 4
Fig. 4. TGA/DSC curves of Fe3−xBixO4 (top) and Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii) (bottom).
Fig. 5
Fig. 5. Magnetization curves of (a) Fe3−xBixO4, (b) Fe3−xBixO4/SiO2, (c) Fe3−xBixO4/SiO2@l-Arg, (d) Fe3−xBixO4/SiO2@l-ArgEt3+I− and (e) Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Fig. 6
Fig. 6. XPS survey spectra of Fe3−xBixO4-SiO2@l-ArgEt3+I− Zn(ii) (a) and high-resolution XPS spectra of Fe 2p (b), Bi 4d (c), O 1s (d), Si 2p (e), N 1s (f), I 3d (g), Zn 2p (h), and C 1s (i).
Fig. 7
Fig. 7. Nitrogen adsorption/desorption isotherms (top) and pore size distribution (down) of nano Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Fig. 8
Fig. 8. EDAX analysis of the reused Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Fig. 9
Fig. 9. FESEM images of the recovered Fe3−xBixO4/SiO2@l-ArgEt3+I−/Zn(ii).
Scheme 3
Scheme 3. Proposed mechanism for the formation of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepines.
See this image and copyright information in PMC

References

    1. Strecker A. Justus Liebigs Ann. Chem. 1850;75:27–45.
    1. Kouznetsov V. V. Galvi C. E. P. Tetrahedron. 2018;74:773–810.
    2. Weber L. Drug Discovery Today. 2002;7:143–147. - PubMed
    1. Eckert H. Molecules. 2012;17:1074–1102. - PMC - PubMed
    2. Brauch S. van Berkel S. S. Westermann B. Chem. Soc. Rev. 2013;42:4948–4962. - PubMed
    3. Rotstein B. H. Zaretsky S. Rai V. Yudin A. K. Chem. Rev. 2014;114(16):8323–8359. - PubMed
    4. Cioc R. C. Ruijter E. Orru R. V. A. Green Chem. 2014;16:2958–2975.
    1. Ruijter E. Orru R. V. A. Drug Discovery Today. 2018;29:1–2. - PubMed
    2. Younus H. A. Al-Rashida M. Hameed A. Uroos M. Salar U. Rana S. Khan Kh. M. Expert Opin. Ther. Pat. 2021;31:267–289. - PubMed
    1. Ahmadi T. Mohammadi Ziarani G. Gholamzadeh P. Mollabagher H. Tetrahedron: Asymmetry. 2017;28:708–724.
    2. Nunes P. S. G. Vidal H. D. A. Corrêa A. G. Org. Biomol. Chem. 2020;18:7751–7773. - PubMed