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Choline chloride based thiourea catalyzed highly efficient, eco-friendly synthesis and anti-bacterial evaluation of some new 6-amino-4-aryl-2,4-dihydro-3-phenyl pyrano [2,3-c] pyrazole-5-carbonitrile derivatives

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Abstract

In this study, a simple and highly efficient synthesis of some new 6-amino-4-aryl-2,4-dihydro-3-phenyl pyrano [2,3-c] pyrazole-5-carbonitrile derivatives by one-pot, four-component reaction with aryl aldehydes, hydrazine hydrate, ethyl benzoylacetate and malonitrile has been achieved. This method provides many advantages such as shorter reaction time with high yields, mild reaction conditions and environmental friendliness. Furthermore, all compounds were subsequently evaluated for their in-vitro antibacterial activity compared with cefazolin by minimum inhibitory concentration, all of these compounds were more active than cefazolin. The characterization of the synthesized compounds was established by melting point, IR, 1H NMR and 13C NMR spectra.

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Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Islamic Azad University-Tehran North Branch.

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Authors and Affiliations

  1. Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran

    Masoumeh Gholami Dehbalaei, Naser Foroughifar & Hoda Pasdar

  2. Young Researchers and Elites Club, Yadegar-e Imam Khomeini (RAH) Branch, Islamic Azad University, Tehran, Iran

    Alireza Khajeh-Amiri

  3. Division of Diabetes, Endocrinology and Metabolism, Faculty of Medicine, Imperial College, London, W12 ONN, UK

    Neda Foroughifar

  4. Department of Chemistry, Ilam Branch, Islamic Azad University, Ilam, Iran

    Mohammad Alikarami

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  1. Masoumeh Gholami Dehbalaei
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  2. Naser Foroughifar
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  4. Alireza Khajeh-Amiri
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  5. Neda Foroughifar
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Correspondence to Naser Foroughifar.

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Dehbalaei, M.G., Foroughifar, N., Pasdar, H. et al. Choline chloride based thiourea catalyzed highly efficient, eco-friendly synthesis and anti-bacterial evaluation of some new 6-amino-4-aryl-2,4-dihydro-3-phenyl pyrano [2,3-c] pyrazole-5-carbonitrile derivatives. Res Chem Intermed 43, 3035–3051 (2017). https://doi.org/10.1007/s11164-016-2810-6

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