Study On The Synthesis Of Isoindolinone Via Benzamide And N-Nitrosoamide Under Visible Light

Isoindolinone is an important molecular skeleton structure in chemical synthesis,which is mainly used in the pharmaceutical field and biological activity field.Its synthesis has attracted the attention of chemists.This dissertation focuses on the modification of isoindolinone at position 3 and reports the construct of isoindolinones prepared from benzamide derivatives.It mainly includes two parts:1.Visible-light-driven synthesis of 3-vinylisoindolinone from amides:We utilized commercially available cobalt salt as a catalyst,dioxygen in the air as a sacrificial reagent,Eosin Y as a photocatalyst,and sodium trimethylacetate hydrate as a base,to prepare 3-vinylisoindolinones from cyclopropenes and benzamides under visible light irradiation.The ring-opening of cyclopropenes and C_sp2-H activation of benzamides under the dual catalytic system provides an inexpensive and mild method for 3-vinylisoindolinone synthesis with the lack of expensive metals.2.Visible-light-driven synthesis of 3-hydroxyimino isoindolinones from N-nitrosoamides.Free radical cyclization and subsequent nucleophilic attacking revealed the conversion from N-nitrosamide derivatives to 3-hydroxyiminoisoindolinone.The reaction is furnished in dichloromethane using methanol as the nucleophilic reagent and visible light as the irradiation source.This system has high reaction efficiency,simple operation,no need for additional additives,and good tolerance to various N-nitrosamide derivatives.There have been few reports on the reactions of N-nitrosamide for decades,and this present reaction provides a useful reference for transformations based on NO chemistry.