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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• 作者：Asadollah Farhadi ; Jalil Noei ; Rasoul Haji Aliyari…
• 关键词：Ionic liquid ; 3 ; 4 ; Dihydropyrimidin ; 2(1H) ; ones ; TiCl3OTf ; [bmim]Cl ; DFT ; Mechanism
• 刊名：Research on Chemical Intermediates
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：42
• 期：2
• 页码：1401-1409
• 全文大小：442 KB
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• 作者单位：Asadollah Farhadi (1)
  Jalil Noei (2)
  Rasoul Haji Aliyari (2)
  Maryam Albakhtiyari (1)
  Mohammad Ali Takassi (1)
  
  1. Petroleum University of Technology, Faculty of Science, 61981-44471, Ahwaz, Iran
  2. Department of Chemistry, Mahshahr Branch, Islamic Azad University, 63519, Mahshahr, Iran
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

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.