Study On The Synthesis Of Coumar In Derivatives And Their Properties

Coumarin is one of the important compounds found in many plants and could beused as the important component of various functional materials. It is well known by itspharmacological, antitumor, anti-inflammatory, anti-coagulant, and anti-oxidantactivities. Some coumarin derivatives have a high fluorescent quantum yield and havebeing widely used as laser dyes, fluorescent probes, solar energy collector and nonlinearoptical dyes. Because of the widely application value of coumarins in the field ofmedicine, pesticide, functional materials an so on, the synthesis of these compounds hasbecome of great interest to synthetic chemists and biologists.In this dissertation, a series of coumarin derivatives has been synthesized bysome simple and efficient methods. Their properties such as fluorescent, recognition ofmetal ions and antitumor activity have been studied. The whole work is mainlycomposed of following four parts:In part one, the research progress and development of the synthesis of coumarinderivatives, the significance and bases of the selection of the subject have beenreviewed.In part two, a series of chromeno[4,3-d]pyrazolo[3,4-b]pyridin derivatives has beeneasily and efficiently synthesized by the reaction of2H-chromen-2-ones withpyrazol-5-amines catalyzed by CuCl2·2H2O in ethanol. These compounds were showedto have high fluorescence quantum yields, which mentioned their value as luminescenceor fluorescence probe. This protocol has the advantages of mild reaction conditions,easy work-up and high yields.In part three, a convenient method has been developed for preparation of5-(2-oxopropyl)-3-chromeno[4,3-d]pyrazolo[3,4-b]pyridine derivatives by the reactionof pyrone, salicylaldehyde and pyrazol-5-amines through one step catalyzed by CuSO4in ethanol. Then we studied on the recognition of metal ions of the synthesized products. The results show that the addition of mental ions have different influence on thefluorescent of compounds. This allowed the potential of quantitative detection of ions.The advantages of this method include high efficiency, mild reaction conditions andconvenient operations.In part four, a series of chromeno[4,3-d]isoxazolo[5,4-b]pyridin derivatives hasbeen easily and efficiently synthesized by the reaction of2H-chromen-2-ones with3-methylisoxazol-5-amine in acetic acid in medium yields. These compounds had anovel heterocyclic skeleton, so we studied the antitumor activity of them. And the resultmentioned their value as potential biological materials. This protocol has the advantagesof material easily available, absence of metallic catalysts and easy work-up.