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Cyclocondensation-Knoevenagel–Michael Domino reaction of phenyl hydrazine, acetoacetate derivatives and aryl aldehydes over acetic acid functionalized ionic liquid

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Abstract

An efficient solvent-free protocol for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five-component condensation reaction of phenyl hydrazine, ethylacetoacetate, and aryl aldehydes in the presence of acetic acid functionalized pyridinium salt (1-(carboxymethyl)pyridinium chloride {[cmpy]Cl}) as reusable catalyst has been reported. Moreover,1 H and13C NMR, mass, CHN analysis, Fourier transform infrared spectroscopy, scanning electron microscope, X-ray diffraction analysis, and calculation of interplaner distance of the catalysts have been studied in this work.

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Acknowledgements

The authors gratefully acknowledge the Bu-Ali Sina University Research Council and Center of Excellence in Development of Environmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) and University of Sayyed Jamaleddin Asadabadi for providing support to this work.

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Authors and Affiliations

  1. Department of Chemistry, Sayyed Jamaleddin Asadabadi University, Asadabad, 6541835583, Iran

    Ahmad Reza Moosavi-Zare

  2. Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Mohammad Ali Zolfigol, Ehsan Noroozizadeh, Omid Khaledian & Behzad Shirmardi Shaghasemi

Authors
  1. Ahmad Reza Moosavi-Zare
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  2. Mohammad Ali Zolfigol
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  3. Ehsan Noroozizadeh
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  4. Omid Khaledian
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  5. Behzad Shirmardi Shaghasemi
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Correspondence to Ahmad Reza Moosavi-Zare or Mohammad Ali Zolfigol.

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Moosavi-Zare, A.R., Zolfigol, M.A., Noroozizadeh, E. et al. Cyclocondensation-Knoevenagel–Michael Domino reaction of phenyl hydrazine, acetoacetate derivatives and aryl aldehydes over acetic acid functionalized ionic liquid. Res Chem Intermed 42, 4759–4772 (2016). https://doi.org/10.1007/s11164-015-2317-6

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