Synthesis Phenanthridines By Fe-catalyzed Radical Reaction Of 2-isocyanobiphenyls

The phenanthridines are significant N-containing heterocycle compounds,which exhibit biological activities and photoelectronic properties.Phenanthridines are not only the important parts of alkaloids with antitumor/antifungal/anticancer abilities but also the skeleton of organic solar cells and molecular probes in the field of material,which means they have great prominent applications.Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls is an efficient access to synthesis different kinds of phenanthridines with diverse radical sources.This dissertation mainly focused on the following three parts:In part one we summarized the achievements of radical reactions to synthesis lots kinds of 6-functionalized phenanthridines from 2-isocyanobiphenyls with different radical sources.These achievements formed the scientific system to guide the paper.In part two we described a novel and efficient route for the synthesis of 6-aroyl phenanthridines on the conditions of 2-isocyanobiphenyl with benzylic alcohol in the presence of MeCN solvent and oxygen using Fe(acac)2 as radical initiator and TBHP as oxidant.The present protocol involves tandem oxidation/intermolecular radical addition/intramolecular radical cyclization/deprotonation/SET sequence in one pot.Besides,we using Fe(II)-Fe(III)catalytic cycle to limit the amont of Iron species,so it can be green environmental protection.In part three we developed a mild oxidative cyclization for the efficient synthesis of 6-methyl phenanthridines using the cheap solvent DMSO as methyl source.In the presence of Fenton reagent as radical initiator and oxidant,benzoic acid as additive,a wide variety of aryl isonitriles were transformed into the corresponding 6-methylated phenanthridines,in moderate to good yields,via an oxidant–cyclization process.The reaction realized the transformation process from C(sp2)– H to C(sp3)– H with cheap readily substrates,which has highly atom enonomy and environmentally friendly.Besides,6-methyl phenanthridines have the properties of easy transformed,which means they can easily synthesis other compounds...