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An efficient three-component one-pot synthesis of 3, 4-dihydropyrimidin-2-(1H)-thione derivatives with a mesoporous iron ion exchanged Indian clay catalyst

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Abstract

This research work focuses on the potential usefulness of iron ion-exchanged Indian bentonite for one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-thiones. Our goal was to produce mesoporous Fe3+-exchanged Indian clay (Fe3+-ExIC) and its supported forms through a wet impregnation technique. The physicochemical properties of the catalysts, such as XRD, FTIR, TGA, physisorption studies, SEM, and acidity, were investigated. It was found that Fe3+-ExIC catalysts are efficient and reusable acidic heterogeneous catalysts for the synthesis of 3,4-dihydropyrimidine-2(1H)-thiones by refluxing aldehyde, methyl acetoacetate and thiourea with acetonitrile in cyclocondensation. An optimized reaction condition was found for preparing 5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione. A possible mechanism for the synthesis of 3,4-dihydropyrimidine-2(1H)-thiones has been proposed. Melting point, FTIR, and proton NMR were used to identify the products. Adequate catalyst activity was maintained over a period of six cycles, and a reduction in activity was attributed to a decrease in the acidity of the recycled catalyst.

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Data will be made available upon reasonable request.

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Acknowledgements

BVK is thankful to the SERB, Ministry of DST, Government of India for sanctioning the research project (Project No. SB/FT/CS-089/2012). The authors thank Vel Tech High Tech Dr. RR Dr.SR Engineering College for providing research facilities.

Funding

The SERB, Ministry of DST, Government of India had provided financial support for this study (Project No. SB/FT/CS-089/2012).

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Authors and Affiliations

  1. Drug Standardization Research Unit, Regional Research Institute of Unani Medicine (NABH & NABL Accredited) (CCRUM, Ministry of AYUSH, Government of India, New Delhi), Chennai, 600013, India

    Mahesh Kancherla

  2. Engineering Department, College of Engineering and Technology, University of Technology and Applied Sciences, P.O. Box 77, 324, Shinas, Sultanate of Oman

    Kondaiah Seku

  3. Department of Chemistry, Vel Tech High Tech Dr. Rangarajan Dr.Sakunthala Engineering College (Autonomous), Avadi, Chennai, 600 062, India

    Mahesh Kancherla & Vijayakumar Badathala

Authors
  1. Mahesh Kancherla
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  2. Kondaiah Seku
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  3. Vijayakumar Badathala
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Contributions

MK: Experimental and Characterization work analysis; KS: Data analysis, Visualization, and Characterization work analysis; VB: Conceptualization, Investigation, Writing-Original Draft, Funding Acquisition.

Corresponding authors

Correspondence to Kondaiah Seku or Vijayakumar Badathala.

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Kancherla, M., Seku, K. & Badathala, V. An efficient three-component one-pot synthesis of 3, 4-dihydropyrimidin-2-(1H)-thione derivatives with a mesoporous iron ion exchanged Indian clay catalyst. Res Chem Intermed 50, 2307–2324 (2024). https://doi.org/10.1007/s11164-024-05247-z

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