Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Jan 4:10:984502.
doi: 10.3389/fchem.2022.984502. eCollection 2022.

Synthesis and characterization of an Fe-MOF@Fe3O4 nanocatalyst and its application as an organic nanocatalyst for one-pot synthesis of dihydropyrano[2,3-c]chromenes

Enayatollah Sheikhhosseini  1 , Mahdieh Yahyazadehfar  1
Affiliations

Synthesis and characterization of an Fe-MOF@Fe3O4 nanocatalyst and its application as an organic nanocatalyst for one-pot synthesis of dihydropyrano[2,3-c]chromenes

Enayatollah Sheikhhosseini et al. Front Chem. .

Abstract

In this study, the recyclable heterogeneous cluster bud Fe-MOF@Fe3O4 'nanoflower' composite (CB Fe-MOF@Fe3O4 NFC) was successfully synthesized using Fe(NO3)3·9H2O, 8-hydroxyquinoline sulfate monohydrate, and Fe3O4 nanoparticles by microwave irradiation. The as-prepared CB Fe-MOF@Fe3O4 NFC was characterized by X-ray diffraction (XRD), field-emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), vibrational sampling magnetometry (VSM), and Fourier transform infrared spectroscopy (FTIR). The CB Fe-MOF@Fe3O4 NFC samples proved to have excellent catalytic activity. The activity of the CB Fe-MOF@Fe3O4 NFC nanocatalyst was explored in the synthesis of dihydropyrano[3, 2-c]chromene derivatives via a three-component reaction of 4-hydroxycoumarin, malononitrile, and a wide range of aromatic aldehyde compounds. Optimized reaction conditions had several advantages, including the use of water as a green solvent, environmental compatibility, simple work-up, reusability of the catalyst, low catalyst loading, faster reaction time, and higher yields.

Keywords: 8-hydroxyquinoline; CB Fe-MOF@Fe3O4 NFC; dihydropyrano[3, 2-c]chromenes; green synthesis; metal–organic framework; reusable catalyst.

PubMed Disclaimer

Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

SCHEME 1
SCHEME 1
Synthesis of CB Fe-MOF@Fe3O4 NFC.
FIGURE 1
FIGURE 1
(A) FE-SEM image, (B) high-resolution FE-SEM image, and (C) TEM image of the CB Fe-hydroxyquinoline@Fe3O4 NFC. Inset: digital image of cluster bud ‘flower’.
FIGURE 2
FIGURE 2
(A) EDX spectra of CB Fe-hydroxyquinoline@Fe3O4 NFC (B) XRD pattern of CB Fe-hydroxyquinoline@Fe3O4 NFC, and (C) VSM magnetization curves of CB Fe-hydroxyquinoline@Fe3O4 NFC.
FIGURE 3
FIGURE 3
IR (KBr, υ/cm−1) curve of (A) Fe3O4, (B) synthesized Fe-MOF, and (C) CB Fe-MOF@Fe3O4 NFC.
SCHEME 2
SCHEME 2
Preparation of 3,4-dihydropyrano[3,2-c]chromenes.
FIGURE 4
FIGURE 4
Recovery of Fe-MOF@Fe3O4 in the synthesis of 2-amino-4,5-dihydro-4-(3- nitrophenyl)-5-oxopyrano[3,2-c]chromen-3-carbonitrile.
SCHEME 3
SCHEME 3
Proposed mechanism of the studied reaction in the presence of CB Fe-hydroxyquinoline@Fe3O4 NFC.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Abdolmohammadi S., Balalaie S. (2007). Novel and efficient catalysts for the one-pot synthesis of 3, 4-dihydropyrano [c] chromene derivatives in aqueous media. Tetrahedron Lett. 48, 3299–3303. 10.1016/j.tetlet.2007.02.135 - DOI
    1. Asadbegi S., Bodaghifard M. A., Mobinikhaledi A. (2020). Poly N, N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: A novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines. Res. Chem. Intermed. 46, 1629–1643. 10.1007/s11164-017-3200-4 - DOI
    1. Asadpour B S., Sheikhhosseini E., Ahmadi S. A., Ghazanfari D., Akhgar M. (2020). Mefenamic acid as environmentally catalyst for threecomponent synthesis of dihydropyrano[2, 3-c]chromene and Pyrano[2, 3-d]pyrimidine derivatives. J. Appl. Chem. Res. 14, 63–73.
    1. Ashraf M. A., Liu Z., Peng W. X., Gao C. (2019). New copper complex on Fe3O4 nanoparticles as a highly efficient reusable nanocatalyst for synthesis of polyhydroquinolines in water. Catal. Lett. 150, 683–701. 10.1007/s10562-019-02986-2 - DOI
    1. Badiei A., Azizi M., Zarabadi P. (2011). Synthesis of 3, 4-dihydropyrano [c] chromene derivatives using sulfonic acid functionalized silica (SiO2PrSO3H). Iran. J. Chem. Chem. Eng 30, 59–65.

LinkOut - more resources