Study On The Synthesis Of Pyrrole [3,4-d]pyrimidinones And Pyrrole [3,4-b]Quinolinones

The dissertation mainly involves the following two aspects: 1.the synthesis of pyrrolo[3,4-d]pyrimidinones;2.the synthesis of pyrrolo[3,4-b]quinolines.1.The synthesis of pyrrolo[3,4-d]pyrimidinones.Dihydropyrimidin-2(1H)-ones(DHPMs)has a wide range of biological activities,including antimicrobial,anti-inflammatory,anti-HIV etc.The Biginelli reaction is a major method to the synthesis of DHPMs.At present,most of publications involving the synyhesis of these compounds focus on changes of the catalyst type.However,reports on the derivatization reaction of DHPMs are less.Hence,the development of simple and efficient new method to synthesize DHPMs is of great significance.In this part,we use DHPMs as raw materials and develop a new method to novel domino allylic C(sp~3)-H aminative cyclization/oxidation reaction that is efficiently catalyzed by copper(I)to directly generate structurally diverse 2H-pyrrolo[3,4-d]pyrimidine-2,5,7(3H,6H)-trione derivatives from DHPMs in a single step in good to excellent yields.Through controlling the experiment,we put forward the possible reaction mechanism.With the characteristics of cheap and accessible raw material sources and using copper salt which is cheap and available,non-toxic and harmless,stable in air and water as catalyst,this method has become a new way to synthesize pyrrolo[3,4-d]pyrimidinones.2.The synthesis of pyrrolo[3,4-b]quinolinones.Pyrrolo[3,4-b]quinoline-based molecules such as camptothecin,mappicine,quinocitrinines A and B have a wide variety of biological activities such as antiviral,antimicrobial,and antitumor activity etc.In general,most of these compositions rely on multi-step methodologies.To the best of our knowledge,to date,there are no reports concerning on synthesizing pyrrolo[3,4-b]quinolinones via direct C(sp~3)-H functionalization/C-N formation strategy.In this part,we present our recent efforts toward the Cu(I)-catalyzed intramolecular tandem C(sp~3)-N cross-coupling and successive oxidation reaction for the preparation of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones in DMSO.The advantages of this method are: raw materials are cheap and accessible,production rate is high and the universality of this reaction is better.Compared with other C(sp~3)-H functionalization,this method not only avoids the use of noble metal catalysts such as palladium,rhodium,rythenium and reduces the costs,improves the economy of the atom.