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CeO2/ZrO2 as green catalyst for one-pot synthesis of new pyrano[2,3-c]-pyrazoles

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Abstract

Ceria-doped zirconia (CeO2/ZrO2)-catalyzed synthesis of pyrano[2,3-c]-pyrazoles via four-component reaction of malononitrile, hydrazine hydrate, ethyl acetoacetate, and substituted aldehydes is described. The catalytic material CeO2/ZrO2 was prepared and characterized by different techniques including powder X-ray diffraction (P-XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and Brunauer–Emmett–Teller (BET) analysis. Twelve new pyrano[2,3-c]-pyrazole derivatives (5a–k) were synthesized in good to excellent yield (89–98%) and their structures established and confirmed by different spectroscopic methods, viz. 1H, 13C, and 15N nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The environmental benefits of the process include excellent yield, short reaction time, simple work-up, elimination of toxic solvents, and avoidance of chromatographic separation. The CeO2/ZrO2 catalyst enables a facile synthesis procedure, is inexpensive, and has good reusability (at least six times).

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Acknowledgements

The authors are grateful to the National Research Foundation (NRF) of South Africa and University of KwaZulu-Natal, Durban for financial support and research facilities.

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Authors and Affiliations

  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban, 4000, South Africa

    Surya Narayana Maddila, Suresh Maddila, Werner E. van Zyl & Sreekantha B. Jonnalagadda

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  1. Surya Narayana Maddila
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  2. Suresh Maddila
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  3. Werner E. van Zyl
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  4. Sreekantha B. Jonnalagadda
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Correspondence to Sreekantha B. Jonnalagadda.

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Maddila, S.N., Maddila, S., van Zyl, W.E. et al. CeO2/ZrO2 as green catalyst for one-pot synthesis of new pyrano[2,3-c]-pyrazoles. Res Chem Intermed 43, 4313–4325 (2017). https://doi.org/10.1007/s11164-017-2878-7

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