Synthesis Of 2-hydroxyphenyl Polyphenyl Ketone And Dibenzophenanthridone Compounds By Photochemical Reaction

Aromatic fused heterocyclicesubstances are important components of organic compounds,which are more diverse and widely used.The2-hydroxybenzaIdehyde moiety and corresponding derivatives are mainly found in certain natural products and have attracted extensive interest due to their applications in the pharmaceutical,dye,cosmetic,such as medicine for cardiovascular diseases.2-hydroxy-4-methoxybenzophenone(OB)is a major component of commercial sunscreens.(2-hydroxyphenyl)(fusedphenyl)ketones are similar to their structuresand have attracted the interest of many chemical researchers due to their potential pharmacological activities and wide application.Phenanthridines are alkaloids containing nitrogen atoms,which have good physiological activities,such as anti-HIV,anti-tumor,etc.Therefore,it has great significance to explore the synthesis of these two types of-compounds.In the first part of this thesis.the main application and synthesis methods of 2-hydroxybenzophenones and diaryl phenanthridine compounds are introduced.Secondly,the types of photochemical reactions are summarized.Finally.the background and research of this paper are briefly explained.In the second part of this thesis,the synthesis of(2-hydroxyphenyl)(fusedphenyl)ketoneswas explored.First,2'-phenylisoflavonewas synthesized and then used as raw light materialtoexplore the reaction conditions for synthesizing(2-hydroxyphenyl)(fusedphenyl)ketones by intramolecular light rearrangement.The optimal conditions for the synthesis of(2-hydroxyphenyl)(fusedphenyl)ketones weredetermined by screening the experimental conditions such as concentration and time of the reaction.It was concluded that theoptimal conditions were irradiation of 2'Pphenylisoflavone(5 mM)in EtOH witha high-pressure mercury lamp(500 W)under an argon atmosphere for 3.0 hours at room temperature.In the study,a total of-27(2-hydroxyphenyl)(fused phenyl)ketones,which were not reported in the literature.were obtained under optimal conditions.All structures were determined by FT-IR,1H NMR,13C NMR?19F NMRand HRMS.Second,the application of light rearrangement products was explored.Finally,the mechanism of the reaction was discussed by literature speculation.In the third part of this thesis?the synthesis of dibenzophenanthridinoneswas discussd.Firstly,the 3,4-diarylquinolinone was used as raw light material to explore the reaction conditions for synthesizing dibenzophenanthridinones by intramolecular photocyclization dehydrogenation.The optimal conditions for the synthesis of dibenzophenanthridinoneswere determined by screening the experimental conditions.lt was concluded that theoptimal conditions were irradiation of 3,4-diarylquinolinone(5 mM)in CHC13 witha high-pressure mercury lamp(500 W)under an argon atmosphere.A series of dibenzophenanthridinoness are synthestized under optimal conditions.All structures are determined by FT-IR,IH NMR,I3C NMR and HRMS.Finally,the mechanism of the reaction was discussed.In this paper,the(2-hydroxyphenyl)(fusedphenyl)ketones and dibenzophenanthridinones are synthesized by photochemical reaction using 2'-aryl isoflavones and 3,4-diarylquinolinones as raw materials.Compared with other methods for synthesizing these two kinds of compounds reported in the literature,notable advantages of our strategy:(1)mild reaction conditions;(2)operational simplicity;(3)it is transition-metal/catalyst free and environmental friendliness.