The Tony Porphine Structural Model In Bc Bipyrrole Synthesis Of The Structural Unit

Tolyporphin is a kind of naturally cyclic tetrapyrroles which have many kinds of biological activities.It plays an important role on anti-tumour treatment,chemical treatment and phototherapy of cancer so the research on its synthesis and application is presently an important study content and hotspots of the chemistry of natural products.In this dissertation,the methods to synthesize tolyporphin model and its segments were summarized through the analysis and comparison to various synthesis methods of chlorins and pyrrole derivatives.The total synthesis way of the tolyporphin model was designed according to the "3+1" synthesis method.The synthesis of two pyrrole derivatives and a dipyrrylmethene were studied,that were the ring-B,C building block of the tolyporphin model—3-methyl-2-oxygen mixed-1H-pyrrole and ethyl 3-bromo-5-formyl-4-methyl-1H-pyrrole-2-carboxylate,and B-C building block of the tolyporphin model-(Z)-ethyl 3-bromo-4-methyl-5-((4-methyl-5-oxo-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrole-2-carboxylate.The synthesis of B-C-semichlorin was prepared with ring B which has Alpha position vacancy and ring C which has Alpha position linked with the formacyl under the alkalinity condition,ring B building block was produced with diethyl oxalacetate and aminoacetone through the Knorr condensation,then by way of decarboxyl and the oxidation,the total yield of ring B was 20.4%;ring C building block was prepared from raw materials such as acetoacetic ester,ethyl-formiate and methyl ethyl ketone through the nitrosation,the claisen condensation,Knorr condensation and then bromination and the formylation,the total yield of ring C was 46.4%.The structures of the synthetic products were characterized by infrared,~1H nuclear magnetic resonance,gas chromatography and mass spectra.The results came to the following conclusions:the synthesis ways of the target compounds were scientific, rational and brief,also had mild reaction conditions.