Synthesis Of Phenanthridine And Phenanthrene Derivatives By Cyclization Of Aliphatic Aldehyde And Phenylboric Acid As Free Radical Precursors

Polycyclic aromatic hydrocarbons are a class of very important compounds,which are widely found in natural products,bioactive structures and medically related compounds,and play an important role in the basic fields of materials science,organic chemistry and pharmaceutical chemistry.In recent years,the free radical insertion reaction has become an efficient and powerful strategy for the construction of complex ring compounds,such as phenanthrene,indoles,phenidines,quinolines and isoquinolines.Although the synthesis methods of carbon cyclic compounds are various,how to use cheap free radical precursors to synthesize thick cyclic compounds has attracted people's attention.Phenanthrene compounds and phenidine compounds were synthesized by using cheap free radical precursors benzoic acid and aliphatic aldehyde.The thesis is divided into two parts.The first part:A series of 6-alkyl phenidine compounds can be rapidly synthesized by using aliphatic aldehyde as the precursor of alkyl radical with 2-isonitrile biphenyl at 130?.The reaction is initiated by FeSO4/DTBP and chlorobenzene as solvents.This reaction tolerates a wide range of functional groups and the scalability is very well.We use of cheap metal salt as catalyst and cheap free radical precursor accords with the concept of green and economic chemistry.The second part:A method for the synthesis of dimethyl phenanthrene-9,10-dicarboxylate by phenylboric acid with dimethyl acetylene dicarboxylate under potassium persulfate and silver carbonate as catalyst is developed,the molecule has thermodynamically stable conformation.This synthetic method has never been introduced,compared with the methods which has be reported the synthesis of phenanthrene,In this method,phenylboric acid was used as a radical precursor for the first time to produce radical cyclization and addition reaction with alkyl ester.The reaction has the advantages of low catalytic dose,mild reaction conditions and short reaction time,which provides a new idea for the synthesis of phenanthrene compounds.Figure 48 table 8 reference 96...