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2008-05-26 - Article/Dans un journal avec peer-review - Anglais - 8 page(s)

Legeay J.-C., Vanden Eynde Jean-Jacques , Bazureau J.P., "Ionic Liquid Phase Organic Synthesis (IoLiPOS) Methodology Applied to the Preparation of New 3,4-Dihydropyrimidine-2(1H)-ones Bearing Bioisostere Group in N-3 Position" in Tetrahedron, 64, 22, 5328 – 5335

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

Abstract(s) :

(Anglais) The ionic liquid phase organic synthesis (IoLiPOS) methodology has been used for the preparation of new 3,4-dihydropyrimidine-2(1H)-ones (DHPMs) bearing bioisostere group in N-3 position. For the 3,4-DHPMs substituted with various thiazole rings, the strategy involved a three-component Biginelli condensation in the second step with good yields (93–96%) from ILP bound acetoacetate, aromatic aldehyde (93–97% yield), and N-methyl urea followed by N-3 alkylation with chloroacetonitrile on the ILP bound 3,4-DHPM. Quantitative thionation of the nitrile group grafted on the ILP bound 3,4-DHPM was realized in MeOH with a 40–48% solution of ammonium sulfide and subsequent addition of a-bromoketone produced the thiazole ring appended on the 3,4-DHPM core. After cleavage by transesterification, the target compounds were obtained in good overall yields (47–50%). The efficiency of the IoLiPOS methodology was also demonstrated by the preparation of new 3,4-DHPMs with a tetrazole ring in N-3 position in 5 steps (53–61% overall yield) via the ILP bound 3-cyanomethyl 3,4-DHPM as key intermediate.

Identifiants :
  • DOI : 10.1016/j.tet.2008.03.021