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Synthesis, characterization and application of nano-silica@[DPSSP][Cl]2 as a novel organic–inorganic hybrid catalyst for the rapid condensation of aldehyde, ammonium acetate and thiobarbituric acid

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Abstract

At first, the preparation and identification of a novel heterogeneous organic–inorganic hybrid acidic nanocatalyst, namely 1,3-(4-pyridyl-1-ium sulfonic acid) (4′-pyridyl-1-ium silica-n-propyl)-propane-dichloride grafted on nano-silica (nano-silica@[DPSSP][Cl]2), have been reported; the identification has been done through a broad range of physicochemical methods comprising FT-IR, SEM, HRTEM, BET, TGA, XRD and EDX techniques. Afterward, nano-silica@[DPSSP][Cl]2 was successfully applied to facilitate the condensation of aryl aldehydes (1 mmol), 2-thiobarbituric acid (2 mmol) and NH4OAc (1.4 mmol) in water solvent (2 mL) at room temperature, such that it provided ten derivatives of pyrido[2,3-d:6,5-d']dipyrimidines (1a–10a) in 5–10 min with yields of 93–99%. Our catalyst furnished the derivatives in very short reaction times and in excellent yields, high atom economy, easy workup and very favorable turnover number (TON) and turnover frequency (TOF) values. In addition, the heterogeneous nature of the catalyst was confirmed and measured using the hot filtration test and its excellent reusability in six runs.

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Acknowledgements

The authors are grateful to acknowledge the Takin Shimi Sepanta Industries Co., Ilam, Iran.

Funding

The authors have no relevant financial or non-financial interests to disclose.

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Authors and Affiliations

  1. Senior Researcher, Engineering School, Central Asian University, 264, Milliy bog street, Tashkent, 111221, Uzbekistan

    Sherzod Shukhratovich Abdullaev

  2. Senior Researcher, Scientific and Innovation Department, Tashkent State Pedagogical University Named After Nizami, Tashkent, Uzbekistan

    Sherzod Shukhratovich Abdullaev

  3. Ph.D. Department of Organic Chemistry, Andijan Machine-Building Institute, Andijan, Uzbekistan

    Sherzod Shukhratovich Abdullaev

  4. Department of Business Administration, Business School, Al Al-Bayt University, P.O.BOX 130040, Mafraq, 25113, Jordan

    Sulieman Ibraheem Shelash Al-Hawary

  5. Al-Zahraa University for Women, Karbala, Iraq

    F. Al-dolaimy

  6. Department of Chemistry, College of Arts and Science, Prince Sattam Bin Abdulaziz University, Wadi Al-Dawasir, 11991, Saudi Arabia

    Raed H. Althomali

  7. Department of Pharmaceutics and Pharmaceutical Technology, College of Pharmacy, Taif University, Taif, Saudi Arabia

    Hashem O. Alsaab

  8. Uttaranchal School of Computing Sciences, Uttaranchal University, Dehradun, 248007, India

    Sheela Bijlwan

  9. Department of Prosthodontics, College of Health and Medical Technology, Al-Ayen University, Thi-Qar, Iraq

    Ibrahim Hammoud Khlewee

  10. College of Technical Engineering, The Islamic University, Najaf, Iraq

    Ahmed Hussien Radie Alawady

  11. College of Technical Engineering, The Islamic University of Al Diwaniyah, Al Diwaniyah, Iraq

    Ahmed Hussien Radie Alawady

  12. College of Technical Engineering, The Islamic University of Babylon, Babylon, Iraq

    Ahmed Hussien Radie Alawady

  13. College of Technical Engineering, Imam Ja’afar Al‐Sadiq University, Al‐Muthanna, Al‐Muthanna, 66002, Iraq

    Ali Hashiem Alsaalamy

  14. Takin Shimi Sepanta Industries Co, Sirvan Industrial Zone, Ilam, PO 6958140120, Iran

    Rohollah Fathollahi

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  1. Sherzod Shukhratovich Abdullaev
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Contributions

S.S.A. synthesized some pyrido[2,3-d:6,5-d']dipyrimidine derivatives (1a–6a) and wrote the manuscript. S.I.S.A. synthesized some pyrido[2,3-d:6,5-d']dipyrimidine derivatives (7a–10a) and helped to edit the manuscript. F.A. identified the structure of some pyrido[2,3-d:6,5-d']dipyrimidine derivatives by 1H NMR, 13CNMR, FT-IR and mass and analyzed their resulting data (1a, 2a and 10a). R.H. optimized the synthesis conditions of pyrido[2,3-d:6,5-d']dipyrimidine derivatives. H.O. identified the structure of the catalyst by means of FE-SEM, HRTEM and EDS analyses. S.B. identified the structure of the catalyst by means of FT-IR and TGA analyses. I.H.K. identified the structure of the catalyst by means of BET and XRD analyses. A.H.R.A. identified the structure of some pyrido[2,3-d:6,5-d']dipyrimidine derivatives by 1H NMR and 13CNMR (4a, 6a and 9a) and analyzed their resulting data. A.H.A. assisted in writing and editing the manuscript. R.F. synthesized the catalyst and helped to edit the manuscript.

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Correspondence to Rohollah Fathollahi.

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Abdullaev, S.S., Al-Hawary, S.I.S., Al-dolaimy, F. et al. Synthesis, characterization and application of nano-silica@[DPSSP][Cl]2 as a novel organic–inorganic hybrid catalyst for the rapid condensation of aldehyde, ammonium acetate and thiobarbituric acid. Res Chem Intermed 50, 723–743 (2024). https://doi.org/10.1007/s11164-023-05162-9

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