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High-efficient synthesis of 2-imino-2H-chromenes and dihydropyrano[c]chromenes using novel and green catalyst (CaO@SiO2@AIL)

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Abstract

In this work, 1,3,5,7-tetraazaadamantan-1-ium chloride (AIL) functionalized silica-coated calcium oxide hybrid nanocatalyst (CaO@SiO2@AIL) as a novel, efficient, green and recyclable heterogeneous ionic liquid catalyst was synthesized. Catalytic activity of the CaO@SiO2@AIL hybrid nanoparticles was investigated for synthesis of the pharmaceutically valuable 2-imino-2H-chromene and dihydropyrano[c]chromene derivatives. A wide range of amines and aromatic aldehydes containing either electron-withdrawing or electron-donating substituent were examined using optimized conditions to produce the desired products. 2-Imino-2H-chromenes were synthesized under solvent-free condition, and dihydropyrano[c]chromenes were prepared in aqueous medium as green conditions within short reaction times, high yields and using easy workup procedures. Structure confirmation and surface properties of the core/shell hybrid nanoparticles were considered via Fourier transform infrared spectroscopy, X-ray powder diffraction, scanning electron microscope, energy-dispersive X-ray spectroscopy, WDS map scan, thermogravimetric and elemental analyses. This IL-supported heterogeneous nanocatalyst can be reused at least six times without considerable loss of its performance.

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Acknowledgements

We gratefully acknowledge the financial support of this work by the research council of Arak University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Arak University, Arāk, 38156-88138, Iran

    Fatemeh Sameri, Akbar Mobinikhaledi & Mohammad Ali Bodaghifard

  2. Institute of Nanosciences and Nanotechnology, Arak University, Arāk, 38156-88138, Iran

    Fatemeh Sameri, Akbar Mobinikhaledi & Mohammad Ali Bodaghifard

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  1. Fatemeh Sameri
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  2. Akbar Mobinikhaledi
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  3. Mohammad Ali Bodaghifard
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Correspondence to Akbar Mobinikhaledi.

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11164_2020_4295_MOESM1_ESM.docx

Supporting information includes detailed information about the experimental procedures, FT-IR, 1HNMR, 13CNMR spectra and elemental analysis of some of new compounds. (DOCX 1760 kb)

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Sameri, F., Mobinikhaledi, A. & Bodaghifard, M.A. High-efficient synthesis of 2-imino-2H-chromenes and dihydropyrano[c]chromenes using novel and green catalyst (CaO@SiO2@AIL). Res Chem Intermed 47, 723–741 (2021). https://doi.org/10.1007/s11164-020-04295-5

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