Study On The Cu(â… ) Catalyzed Substitution/coupling Cascade Reaction And Pilot Study On The Sm(â…¢) Reagent Mediated"Ester-allene" Coupling Reaction

The first part of this paper developed a novel copper-catalyzed synthesis of a variety of substituted quinoline/pyridine, thiochromene and naphthalene derivatives through domino SN2’/coupling, SN2’/deacylation/coupling and SN2’/coupling/elimination reactions. These cyclic products might be of biological and medicinal value. The method provides a general and convenient approach to various substituted cyclic compounds from the corresponding Baylis-Hillman acetates (B-H acetates) and N-/S/C-nucleophiles.The second part investigated novel "ester-alkene" coupling reactions using allySmBr/HMPA/H2O system. Thus the esters of homoallylic alcohols underwent cascade cyclization and afforded a variety of2-(2-hydroxyl alkyl)propanol derivatives in reasonable yields and good stereoselectivity. The conditions were further optimized, and it was found that allySmBr-HMPA-(EtO)2P(O)H system could improve the yields to a certain extent. Using this system, the alkenyl propanol compounds were obtained in better yields. The possible mechanism of the reaction was studied and the isolation of the intermediate allowed the proposal of a probable mechanism...