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Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control

Nematpour, M ; Sharif University of Technology | 2018

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  1. Type of Document: Article
  2. DOI: 10.1080/17415993.2017.1402332
  3. Publisher: Taylor and Francis Ltd , 2018
  4. Abstract:
  5. An efficient one-pot regioselective synthesis of various novel 3,4-dihydropyrimidin-2(1H)-one (DHPMs) via a three-component Biginelli-type condensation of aldehyde, phenylacetone and urea/thiourea under two different based-catalyzed conditions is described. In kinetic control path, lithium N, N-diisopropylamide (LDA-20 mol % generated in situ from n-BuLi and diisopropylamine) was used as the base, in tetrahydroforane (THF) as the solvent at 0°C. Thermodynamic control path was run with NaH as the base, in EtOH as the solvent under reflux status. The simple procedure, mild base-catalytic reaction conditions, no column chromatography and good to high yields are important features of this protocol. © 2017 Informa UK Limited, trading as Taylor & Francis Group
  6. Keywords:
  7. 3,4-Dihydropyrimidin-2(1H)-one ; Biginelli- type ; Kinetic-thermodynamic ; Lithium N,N-diisopropylamide ; Phenylacetone ; Urea/thiourea
  8. Source: Journal of Sulfur Chemistry ; Volume 39, Issue 2 , 2018 , Pages 151-163 ; 17415993 (ISSN)
  9. URL: https://www.tandfonline.com/doi/abs/10.1080/17415993.2017.1402332?journalCode=gsrp20