Synthesis of Some New 3-Pyrrolidinylquinoline Derivatives via 1,3-Dipolar Cycloaddition of Stabilized Azomethine Ylides to Quinolinyl α,β- Unsaturated Ketones

Abdelmalek Bouraiou (1) , Abdelmadjid Debache (1) , Salah Rhouati (1) , Ali Belfaitah (1) , N. Benali-Cherif (2) , Bertrand Carboni (3)

1 PHYSYNOR - Laboratoire des produits naturels d'origine végétal et de synthèse organique
2 Laboratoire des Structures, Propriétés et Interactions Inter Atomiques
3 ISCR - Institut des Sciences Chimiques de Rennes

N-Metallated azomethine ylide generated from methyl (E)-N-benzylideneglycinate, LiBr and triethylamine underwent cycloaddition to quinolyl α,β- unsaturated ketones with excellent diastereoselectivity to afford new functionalised 3-pyrrolidinylquinoline derivatives.

Mots clés: 3-dipolar cycloaddition; quinoline; pyrrolidine synthesis; azomethine ylides

Domaines: Chimie organique

Abdelmalek Bouraiou, Abdelmadjid Debache, Salah Rhouati, Ali Belfaitah, N. Benali-Cherif, et al.. Synthesis of Some New 3-Pyrrolidinylquinoline Derivatives via 1,3-Dipolar Cycloaddition of Stabilized Azomethine Ylides to Quinolinyl α,β- Unsaturated Ketones. Open Organic Chemistry Journal, 2010, 4, pp.1-7. ⟨hal-00869747⟩