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Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process

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Abstract

This paper presents the efficient synthesis of 2-amino-4H-benzo[b]pyrans using mesoporous poly-melamine-formaldehyde as a polymeric heterogeneous catalyst. According to the principals of green chemistry, the reaction was performed by the planetary ball milling process at ambient and neat conditions. The heterogeneous catalyst could be reused up to five runs with no reducing of catalytic efficiency. A variety of substituted 2-amino-4H-benzo[b]pyrans were obtained in good to excellent yields under eco-friendly conditions. Other advantages of the current methodology include short reaction time, wide substrate-scope, and use of a metal-free polymeric catalyst. Also, the current method avoids the use of hazardous reagents and solvents, tedious workup and multi-step purification. This work revealed that porous organic polymers containing Lewis base sites having acceptor-donner hydrogen bonding functional groups, and high porosity could play a vital role in the promotion of the one-pot multicomponent reactions in the solid-phase synthesis.

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Acknowledgements

This work was supported by a High Impact Research Grant (NANOCAT RU001-2019) for Scientific Research from University of Malaya, Malaysia. The author is grateful to staff members in the Analytical and Testing Center of Nanotechnology & Catalysis Research Center, University of Malaya for partial support of this work.

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Authors and Affiliations

  1. Nanotechnology and Catalysis Research Center, Institute of Postgraduate Studies, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Lia Zaharani, Nader Ghaffari Khaligh & Mohd Rafie Johan

  2. Environmental Research Laboratory, Department of Water and Environmental Engineering, School of Civil Engineering, Iran University of Science and Technology, 16765-163, Tehran, Iran

    Taraneh Mihankhah

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  1. Lia Zaharani
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  2. Nader Ghaffari Khaligh
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  3. Taraneh Mihankhah
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Correspondence to Nader Ghaffari Khaligh.

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Zaharani, L., Khaligh, N.G., Mihankhah, T. et al. Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process. Mol Divers 25, 323–332 (2021). https://doi.org/10.1007/s11030-020-10092-4

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