DI-UMONS : Dépôt institutionnel de l’université de Mons

Recherche transversale
(titres de publication, de périodique et noms de colloque inclus)
2004-04-19 - Article/Dans un journal avec peer-review - Anglais - 9 page(s)

Hakkou H., Vanden Eynde Jean-Jacques , Hamelin J., Bazureau J.P., "Ionic Liquid Phase Organic Synthesis (IoLiPOS) Methodology Applied to the Three Component Preparation of 2-Thioxo Tetrahydropyrimidin-4(1H)-ones under Microwave Dielectric Heating" in Tetrahedron, 60, 17, 3745 - 3753

  • Edition : Pergamon Press, Oxford (United Kingdom)
  • Codes CREF : Chimie organique (DI1313)
  • Unités de recherche UMONS : Chimie organique (S836)
Texte intégral :

Abstract(s) :

(Anglais) An ionic liquid phase organic synthesis (IoLiPOS) has been developed for the preparation of 2-thioxo tetrahydropyrimidin-4(1H)-ones. Treatment of the starting poly(ethyleneglycol)ionic liquid phases (PEGn-ILPs) 1 with acryloyl chloride 2 afforded a serie of (PEGn)-ILPs bound acrylate 3 in quantitative yields. Michael addition of aliphatic primary amines 5 to the PEG1-ILPs 3(a,d) allowed the preparation of ß-aminoesters 6 in high yields. Addition of alkyl isothiocyanates 7 to 6 gave the corresponding thioureido esters 8 in the third step. The final cyclization-cleavage under microwave/solventless strategy provides, under basic conditions, the expected 2-thioxo tetrahydropyrimidin-4(1H)-ones 9 in high purity after flash chromatography. According to the IoLiPOS methodology, the NMR method was used to establish loading of all the PEG-ionic liquid phases intermediates.

Notes :
  • (Anglais) Lecture en ligne: http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6THR-4C12CC3-3-H&_cdi=5289&_user=532054&_pii=S0040402004003850&_origin=search&_coverDate=04%2F19%2F2004&_sk=999399982&view=c&wchp=dGLbVzW-zSkzS&md5=ec78695cb386d5f887d6ac7bc258f589&ie=/sdarticle.pdf
Identifiants :
  • DOI : 10.1016/j.tet.2004.03.026