Access to substituted thiapyrrolizidinones and fused pyridones using the domino N-acyliminium-thionium equilibrium/1,3-dipolar cycloaddition/desulfurization cyclization cascade

Abdulkareem Hamid (1) , Hassan Oulyadi (2) , Adam Daïch (1)

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Substituted thiapyrrolizidinones and fused pyridones, and quinolizinones were reported efficaciously from suitable thioamides in yields ranging from 30% to 65%. The reaction proceeded in a one-pot procedure as cascade process by the intramolecular 1,3-dipolar cycloaddition of thioisomünchnones followed by desulfurization of the adducts. During these investigations, the mechanistic aspects of the process were also discussed.

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry

Abdulkareem Hamid, Hassan Oulyadi, Adam Daïch. Access to substituted thiapyrrolizidinones and fused pyridones using the domino N-acyliminium-thionium equilibrium/1,3-dipolar cycloaddition/desulfurization cyclization cascade. Tetrahedron, 2006, 62 (26), pp.6398-6404. ⟨10.1016/j.tet.2006.04.032⟩. ⟨hal-02564933⟩