Copper Catalyzed Synthesis Of Imidazo[1,5-a]N Heterocycles Bearing Cyano Group

Aromatic cyano compounds are an important class of organic synthesis intermediates.They can be hydrolyzed to form carboxylic acids or amides and reduced to form amines.They are also of great value in many pharmaceutical molecules,dye molecules and some polymer materials.The synthesis of some aromatic cyano compounds has been relatively mature,but the synthesis of cyanated imidazo[1,5-a]N heterocycles is very rare.In this thesis,the synthesis of two cyanated imidazo[1,5-a]N heterocycles promoted by copper catalysts was developed.The main contents are as follows:Firstly,the paper reviews the application of aromatic cyano compounds in the fields of medicine,pesticides,perfumes,materials and organic synthesis.The importance of such compounds and the necessity of this paper are clarified.Then the paper introduces the research progress of cyanation catalyzed by transition metals such as palladium,copper,cobalt,ruthenium,iron,manganese and ruthenium in recent years.By comparison,copper catalysts have great advantages in terms of price and availability,and the copper-catalyzed cyanation reaction does not require the participation of ligands.Secondly,the paper developed a new method for the synthesis of cyanated imidazo[1,5-a]N heterocycles using stoichiometric copper as catalyst.The catalysts,additives,cyanating reagents and their dosages in the reaction system were optimized.After the optimal conditions were established,the cyanation substrate was expanded and a series of cyanated imidazo[1,5-a]N heterocyclic compounds were synthesized.The phenylacetonitrile used in the reaction is also an environmentally friendly cyanation reagent.Finally,the paper developed a copper-promoted three-component process for the synthesis of 3-cyanoimidazo[1,5-a]quinolines.Methylamines,amino acids and 2-methylquinoline compounds can be used as substrates for the cyanation reaction.A series of cyano substituted imidazo[1,5-a]N quinolines were successfully synthesized by this method.This method has a wide range of substrates and is well tolerated by functional groups and is suitable for small industrial production.Figure [7] table [19] reference [84]...