138984-08-4Relevant articles and documents
Cascade Vinyl Radical Ipso-Cyclization Reactions and the Formation of α,β-Unsaturated-β-aryl-γ-lactams from N-Propargyl Benzamides
Luo, Chih-Hao,Wang, Pei-Ling,Chang, Che-Chien
, p. 15033 - 15044 (2021/10/20)
Various N-(2-bromo-allyl) benzamides were used as the starting materials to study vinyl radical cyclization reactions. The vinyl radicals underwent ipso-cyclization, fragmentation, and cyclization reactions to produce β-aryl-γ-lactams with the carbonyl group remaining intact. To further study this cascade radical reaction, vinyl radicals were generated by the addition of a tributyltin radical to alkyne moieties, followed by radical ipso-cyclization, fragmentation, cyclization, and β-scission reactions with the production of a series of α,β-unsaturated-β-aryl-γ-lactam derivatives. This new type of radical reaction was examined from the substituent effects on both the amino groups and the aryl groups. A bulky tert-butyl substituent on the amino group enhanced the formation of a Z-conformation of the benzamides and facilitated vinyl radical ipso-cyclization reactions. A synthetic method for preparing α,β-unsaturated-β-aryl-γ-lactams from N-propargyl benzamides was developed.
Control of Chemoselectivity in Catalytic Carbenoid Reactions. Dirhodium(II) Ligand Effects on Relative Reactivities
Padwa, Albert,Austin, David J.,Hornbuckle, Susan F.,Semones, Mark A.,Doyle, Michael P.,Protopopova, Marina N.
, p. 1874 - 1876 (2007/10/02)
-
