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An alternative, practical, and ecological protocol for synthesis of arylidene analogues of Meldrum’s acid as useful intermediates

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Abstract

This paper presents an ecological protocol for Knoevenagel condensation using a catalytic amount of 4,4′-trimethylenedipiperidine as a versatile, efficient, safe, commercially available, inexpensive, and recyclable organocatalyst by a ball-milling process at room temperature. The scope of the present protocol was explored and demonstrated for Knoevenagel condensation of the active methylene, such as Meldrum’s acid with various aryl and heteroaryl aldehydes. The developed protocol provides a good to excellent conversion of various aldehydes to respective Knoevenagel products in an environmentally friendly process. Furthermore, this efficient process displays a combination of the synthetic virtues of conventional Knoevenagel condensation with ecological benefits and the convenience of a facile mechanochemistry procedure.

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Acknowledgements

The authors are grateful to staff members at the Analytical and Testing Center of Research House of Professor Reza, and express thanks to the 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, 3rd Floor, Block A, 50603, Kuala Lumpur, Malaysia

    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. Nader Ghaffari Khaligh
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  2. Taraneh Mihankhah
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  3. Mohd Rafie Johan
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Correspondence to Nader Ghaffari Khaligh.

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Khaligh, N.G., Mihankhah, T. & Johan, M.R. An alternative, practical, and ecological protocol for synthesis of arylidene analogues of Meldrum’s acid as useful intermediates. Res Chem Intermed 45, 3291–3300 (2019). https://doi.org/10.1007/s11164-019-03796-2

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