Construction Of Phenanthridine Derivatives Via Cascade Radical Reaction Of Functionalized Isocyanides

This thesis is focused on isocyanide-based free radical reaction, which is an efficient method for the construction of phenanthridines through the reaction of isocyanide with easy and accessible radical precursors. The phenanthridines are significant N-containing heterocycle compounds, which exhibit interesting biological activities, drug properties and optoelectronic applications. The whole work is constituted by three parts as follow:The second chapter concentrates on a Ag(I)-promoted radical cascade reaction. A C-C bond and a C-P bond are formed in the synthesis of 6-phosphorylated phenanthridines. This method avoided utilizing stoichiometric amounts of silver salts, which is environmentally friendly.In the third chapter, we have firstly demonstrated a TBPB-mediated cascade cyclization reaction of 2-isocyanobiaryl with commercially available ether via subsequently C(sp3)-H/C(sp2)-H bond functionalization. Notably, the phenanthridines with 1,4-dioxane ring moiety were obtained under mild and metal-free conditions.The forth chapter involves a Mn(III)-mediated reaction of 2-isocyanobiaryls with 1,3-dicarbonyl compounds for the preparation of 6-alkylated and 6-monofluoro-alkylated phenanthridines. The mono-fluoromethylated phenanthridines are obtained by further decarboxylation. This is a practical strategy for constructing fluorine-containing organic molecules.