Ni-catalyzed Tandem Reaction Of Nitrile And Arboric Acid To Construct Nitrogen-containing Heterocyclic Compounds

This thesis reviewed recent progress in the synthesis of carbonyl or heterocyclic compounds from nitriles by metal-catalyzed.Then around this subject,a series of reaction of nitriles and arylboronic acids were developed by non-noble metal(nickel)-catalyzed to construct amino isoquinoline,isoquinolinone,pyrrole,pyridine derivatives.Five chapters are included:Chapter 1,the C-C coupling reaction of nitriles with arylation reagents by transition metals is summarized,and the prospect of this area are also provided.Chapter 2,the nickel-catalyzed tandem coupling / cyclization reaction of o-cyanobenzoacetonitrile and arylboronic acid to synthesize amino isoquinoline compounds was developed.This method presents an efficient procedure that delivers functional amino isoquinoline with highly functional groups toleration.Chapter 3,the nickel-catalyzed tandem coupling / cyclization reaction of methyl o-acetonitrile benzoate and arylboronic acid was studied to synthesize isoquinolinone compounds.This method prossess some advantages,such as mild reaction condition,green solvents and available sustrates.In addition,the reaction is further applied to the synthesis of a biologically active substance.The possible mechanism of the reaction is discussed.Chapter 4,the nickel-catalyzed tandem addition / cyclization reaction of alkylacetonitrile-based substrate with arylboronic acid was studied to synthesize asymmetric 2,5-diarylpyrroles and 2,6-diarylpyridines.The method provided novel strategy for the synthesis of pyrrole and pyridine compounds.Chapter 5,is the experimental part.Including experimental general rules,product synthesis steps and structural characterization.