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Effectual and rapid synthesis of bis(pyrazolyl)methanes and pyrazolopyranopyrimidines catalyzed by nano-[TSPSED][Cl]2 and investigating their biological activity

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Abstract

This investigation reports application of a mesoporous nanomaterial based on dicationic ionic liquid bonded to amorphous silica, namely nano-N,N,N′,N′-tetramethyl-N-(silican-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2), as an extremely effectual and recoverable catalyst for the generation of bis(pyrazolyl)methanes and pyrazolopyranopyrimidines in solvent-free conditions. In both synthetic protocols, the performance of this catalyst was very useful and general and presented attractive features including short reaction times with high yields, reasonable turnover frequency and turnover number values, easy workup, high performance under mild conditions, recoverability and reusability in 5 consecutive runs without losing activity. In addition, the antioxidant, antibacterial, and antifungal activity of some synthesized derivatives was studied for the first time. Our investigations showed that most of the studied compounds (2a, 5a, 8a, 11a, 2b and 5b–9b) have the mentioned biological properties.

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Acknowledgements

We are grateful to acknowledge the Research Council of Al-Bayan University, Baghdad, Iraq.

Funding

The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.

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Authors and Affiliations

  1. Department of Materials Engineering, College of Engineering, University of Al-Qadisiyah, Al Diwaniyah, Iraq

    Riyam I. Jaddan & Akeel Hssain Kadium

  2. Dentistry Department, Al-Rasheed University College, Baghdad, 10011, Iraq

    Ali Aqeel Mahmood

  3. Department of Computer Engineering Technology, Al Kitab University, Altun Kopru, Kirkuk, 00964, Iraq

    A. H. Shather

  4. Department of Chemical Engineering and Petroleum Industries, Al-Mustaqbal University College, Hilla, 51001, Iraq

    Alaa Dhari Jawad Al-Bayati

  5. Collage of Pharmacy, National University of Science and Technology, Nasiriyah, Dhi Qar, Iraq

    Murtadha Laftah Shaghnab

  6. Chemistry Department, College of Science, University of Baghdad, Baghdad, Iraq

    Haider Abdulkareem Almashhadani

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  1. Riyam I. Jaddan
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  2. Akeel Hssain Kadium
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  3. Ali Aqeel Mahmood
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Contributions

RIJ did synthesis of all bis(pyrazolyl)methanes derivatives (1a–13a) and helping to edit the manuscript. AHK done synthesis of some pyrazolopyranopyrimidines derivatives (1b–6b) and writing the manuscript. AAM contributed to synthesis of some pyrazolopyranopyrimidines derivatives (7b–10b) and reviewing the manuscript. AHS optimized the synthesis conditions of bis(pyrazolyl)methanes and pyrazolopyranopyrimidines. ADJA-B identified the structure of bis(pyrazolyl)methanes by 1H and 13CNMR, as well as analyzed their resulting data. MLS identified the structure of pyrazolopyranopyrimidines by 1H NMR, 13CNMR, FT-IR, Mass and analyzed their resulting data as well as investigated the biological properties of the produced derivatives. HAA synthesized the catalyst and identified the structure of the catalyst by means of FT-IR, TEM, HR-TEM, FE-SEM, EDX, TGA and XRD analyses.

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Correspondence to Haider Abdulkareem Almashhadani.

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Jaddan, R.I., Kadium, A.H., Mahmood, A.A. et al. Effectual and rapid synthesis of bis(pyrazolyl)methanes and pyrazolopyranopyrimidines catalyzed by nano-[TSPSED][Cl]2 and investigating their biological activity. Res Chem Intermed 49, 4103–4126 (2023). https://doi.org/10.1007/s11164-023-05060-0

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