Study On The Synthesis Of Benzo[a]phenanthridine And Pyrimido[4,5-b]indole

Benzophenanthridine and pyrimido[4,5-b]indole are two major components of nitrogen-containing heterocyclic compounds,and are closely related to our daily lives.First,the polycyclic aromatic structure fused with benzophenanthridine and pyridine,which is similar to its structure,are widely used in natural alkaloids,medicines,and materials as the central skeleton.For example,benzophenanthridine derivatives are one of the widely distributed alkaloids and are related to DNA strand insertion ability and potent anti-tumor,anti-malarial and antibacterial activities.Secondly,as a component of nucleotides,pyrimidine,its derivatives pyrimidinyl indole and pyrimido indole,play an important role in the application of medicine,and it is the key center body of anti-cancer drugs and anti-AIDS drugs.In the synthesis of drugs,no heavy metal residues and reduction of production costs must be paid attention to.Therefore,the continuous development of new synthetic methods is necessary and extremely meaningful.In this thesis,a one-pot method for the synthesis of benzophenanthridines and pyrimido[4,5-b]indoles with aromatic amines and benzamidine hydrochloride as nitrogen sources was developed,respectively.The main research contents are as follows:1.A three-component “one-pot method” method for synthesizing triphenanthridine compounds using cheap and easily available aromatic amines,benzaldehyde and cyclohexanone as raw materials under the condition of no transition metals has been developed.The reaction involves the dehydroaromatization of cyclohexanone and DA reaction and other steps.The method does not need to use transition metal catalysis.Using KI,methyl phenyl sulfoxide and mixed camphor sulfonic acid as additives can effectively promote the reaction.The raw materials are simple and cheap,and the substrate is widely applicable,which provides for the synthesis of benzophenanthridine a new and practical method.2.Developed a one-pot synthesis of pyrimido[4,5-b]indole and its derivatives using 3-indolecarboxaldehyde and benzamidine hydrochloride as raw materials.The reaction involves C-N condensation,hydrocarbon activation and other steps.The reaction only uses the inexpensive transition metal compound Cu I as a catalyst,bipyridine as a ligand,and common DMSO as an additive.The reaction is efficient and the substrate functional group is well tolerated,which provides a new way for the synthesis of pyrimidine[4,5-b]indole and its derivatives.