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A facile one-pot green synthesis of novel 2-amino-4H-chromenes: antibacterial and antioxidant evaluation

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Abstract

Synthesis of novel derivatives of 2-amino-4H-chromene is reported via three-component reaction of 2,4-dihydroxybenzophenone, malononitrile, and aromatic aldehydes in the presence of catalytic amount of triethylamine in ethanol as a green solvent with high to excellent yields. The structure of the synthesized products was characterized by FTIR, 1H, 13C NMR spectroscopy, CHN analyses, and mass spectrometry. Simplicity of the procedure, green reaction conditions, short reaction time, and easy separation of the products make this an interesting alternative to other reported approaches. Also, their antibacterial and antioxidant activities were evaluated against Staphylococcus aureus as Gram-positive bacteria and Escherichia coli as Gram-negative bacteria through the minimum inhibitory concentration method, as well as the radical scavenger 2,2-diphenyl-1-picrylhydrazyl. Among these compounds, 4b including halogen substituent and 2-amino-4H-pyran moiety showed the highest antioxidant and antibacterial activities.

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Fig. 1
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All spectra data (Copies of the 1H NMR, 13CNMR, MASS and FT-IR data spectra) are included in the supplementary information file.

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Acknowledgements

The authors acknowledge the Research Council of the University of Mazandaran.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran

    Mona Maddahi, Sakineh Asghari & Ghasem Firouzzadeh Pasha

  2. Nano and Biotechnology Research Group, University of Mazandaran, Babolsar, 47416-95447, Iran

    Sakineh Asghari

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  1. Mona Maddahi
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  2. Sakineh Asghari
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Maddahi, M., Asghari, S. & Pasha, G.F. A facile one-pot green synthesis of novel 2-amino-4H-chromenes: antibacterial and antioxidant evaluation. Res Chem Intermed 49, 253–272 (2023). https://doi.org/10.1007/s11164-022-04893-5

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