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

Recherche transversale
(titres de publication, de périodique et noms de colloque inclus)
2007-02-05 - Article/Dans un journal avec peer-review - Anglais - 6 page(s)

Legeay J.-C., Vanden Eynde Jean-Jacques , Bazureau J.P., "A New Approach to N-3 Functionalized 3,4-Dihydropyrimidine-2(1H)-ones With 1,2,4-Oxadiazole Group as Amide Isostere via Ionic Liquid Phase Technology" in Tetrahedron Letters, 48, 6, 1063 – 1068

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

Abstract(s) :

(Anglais) New N-3 functionalized 3,4-dihydropyrimidine-2(1H)-ones with 1,2,4-oxadiazole group as amide isostere were synthesized in six steps by ionic liquid-phase organic synthesis (IoLiPOS) methodology from ILP bound acetoacetate. The 3,4-dihydropyrimidine-2(1H)-one (3,4-DHPM) core was prepared in the first step by one-pot three-component Biginelli condensation followed by N-alkylation with chloroacetonitrile. Then the nitrile group appended on the 3,4-DHPM heterocycle was quantitatively transformed into amidoxime. Addition of aliphatic carboxylic anhydride or aromatic carboxylic acid to the amidoxime produced the expected 1,2,4-oxadiazole via the O-acylamidoxime intermediate grafted on the ILP bound 3,4-DHPM using two convergent methods. After cleavage by transesterification under mild conditions, the target compounds were obtained in good overall yields. The structures and the purities of the reaction intermediates in each step were verified easily by routine spectroscopic analysis.

Identifiants :
  • DOI : 10.1016/j.tetlet.2006.11.148