Research on Chemical Intermediates

, Volume 42, Issue 2, pp 1401–1409 | Cite as

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

  • Asadollah Farhadi
  • Jalil Noei
  • Rasoul Haji Aliyari
  • Maryam Albakhtiyari
  • Mohammad Ali Takassi
Article

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.

Keywords

Ionic liquid 3,4-Dihydropyrimidin-2(1H)-ones TiCl3OTf [bmim]Cl DFT Mechanism 

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Asadollah Farhadi
    • 1
  • Jalil Noei
    • 2
  • Rasoul Haji Aliyari
    • 2
  • Maryam Albakhtiyari
    • 1
  • Mohammad Ali Takassi
    • 1
  1. 1.Petroleum University of TechnologyFaculty of ScienceAhwazIran
  2. 2.Department of Chemistry, Mahshahr BranchIslamic Azad UniversityMahshahrIran

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