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Experimental and theoretical study on a one-pot, three-component route to 3,4-dihydropyrimidin-2(1H)-ones/thiones TiCl3OTf-[bmim]Cl

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Abstract

In this study a synthetic method using TiCl3OTf-ionic liquid was reported for synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones (3,4-DHPMs). Condensation reactions were carried out for aldehydes, ethyl acetoacetate, and ammonium acetate. In the reaction 1-butyl-3-methylimidazolium chloride ([bmim]Cl) was used as an ionic liquid in the presence of TiCl3OTf catalyst under solvent-free conditions at 140 °C. The advantages of this method are high yield of product, short reaction time, and reusable catalyst. A mechanism was proposed for this condensation reaction, and all steps of the suggested mechanism were confirmed by density functional theory calculations using the B3LYP/6-311G level of theory.

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Acknowledgments

The authors are grateful to the Islamic Azad University, Mahshahr branch, and the Petroleum University of Technology for partial support of this work.

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Authors and Affiliations

  1. Petroleum University of Technology, Faculty of Science, 61981-44471, Ahwaz, Iran

    Asadollah Farhadi, Maryam Albakhtiyari & Mohammad Ali Takassi

  2. Department of Chemistry, Mahshahr Branch, Islamic Azad University, 63519, Mahshahr, Iran

    Jalil Noei & Rasoul Haji Aliyari

Authors
  1. Asadollah Farhadi
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  2. Jalil Noei
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  3. Rasoul Haji Aliyari
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  4. Maryam Albakhtiyari
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  5. Mohammad Ali Takassi
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Correspondence to Asadollah Farhadi.

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Farhadi, A., Noei, J., Aliyari, R.H. et al. Experimental and theoretical study on a one-pot, three-component route to 3,4-dihydropyrimidin-2(1H)-ones/thiones TiCl3OTf-[bmim]Cl. Res Chem Intermed 42, 1401–1409 (2016). https://doi.org/10.1007/s11164-015-2092-4

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  • DOI: https://doi.org/10.1007/s11164-015-2092-4

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