Visible Light Catalyzed Synthesis Of Coumarin Compounds From Aryl Propiolate

There are a large number of complex natural product molecules in nature,and nitrogen-containing heterocycles and oxygen-containing heterocycles are important components of complex natural product molecules;It has a wide variety of applications in the fields of medicine,sterilization,insecticide,weeding,plant growth regulation and photoelectric materials.Studies have shown that coumarin and its derivatives(benzopyran ring)have good performance in anti-cancer,anti-inflammatory and anti-coagulation,and can be used as raw materials for dyes and fluorescent probes;some have good anti-tumor,Anti-HIV drugs also contain benzopyran ring drug fragments.Therefore,chemists have been working to develop green,efficient,and inexpensive methods to synthesize heterocyclic compounds,or have modified the reactive sites by activating the heterocyclic compounds.In recent years,due to the high background of green chemistry,such as high reaction efficiency,mild greening of reaction conditions,and high atom utilization,photocatalytic reactions have become more and more popular in organic synthesis.One of the research hotspots.Based on the above research background,the work concludes of three parts:(1).In the first part,this work developed a study of the synthesis of 3-alkylated coumarins based on visible light-induced 4-CzIPN as a photocatalyst.Under blue light irradiation,4-CzIPN catalyzes peroxyacyl to generate alkyl radicals and reacts with aryl alkynyl to form coumarin compounds.The reaction substrate has good adaptability and good reaction results for grades 1,2,and 3 carbons.It is an efficient and green reaction strategy,which provides a feasible way for coumarin alkylation.Wide coumarin molecular library.(2).In the second part,this work develops the synthesis of 3-amide-coumarins by reaction of alkynyl compounds with ketoacid amides under visible light catalysis.In this reaction,alkynyl compounds are used as the reaction substrate,and ketoacid amide is activated by BI-OAc.Under the induction of visible light,4-CzIPN is used as a photocatalyst to obtain amide radicals.This reaction uses a milder reaction condition to make both coumarin and amide,which are both molecularly active,"strongly combined".It provides an efficient,green and high-yield strategy for the amide functionalization of coumarin.