Preparation Of Fused Triazole Compounds And Design,Synthesis And Properties Of Novel Thiopyrone Fluorescent Probes

This thesis contains two parts of work.A new method for the synthesis was explored about 1,2,3-triazole without metal catalysis.Next,the fluorescent probes TCM-1 and TCM-2 were designed and synthesized with benzothiopyranone as the core structure,and the fluorescent probes of optical properties were studied.1,2,3-triazole and its derivatives have become the current research hotspot because of its excellent performance in anti-cancer,antibacterial and other medical research.In this thesis,a new type of metal-free catalyzed carbocation-mediated[3+2]cycloaddition reaction was studied,and polysubstituted 1,2,3-triazole derivatives were synthesized.After multiple screening of reaction conditions,Lewis acid BF₃·OEt₂was selected as the carbocation initiator to carry out intramolecular cycloaddition reaction to synthesize triazole.On this basis,the synthesis of different alkynols as raw materials with fluorenone for coupling,and then with Na N₃nucleophilic reaction to generate azide compounds,through BF₃·OEt₂catalysis to get fluorenone thick triazole derivatives.Through the comparison of various ring conditions,TMSOTf is the best choice for the synthesis of tricyclic fused triazoles.Under the catalysis of TMSOTf,organic azides and different types of acetylenic alcohols undergo intramolecular 1,3-dipolar cycloaddition reactions to synthesize tricyclic fused triazole derivatives with different substituents.This mild carbocation-mediated[3+2]cycloaddition reaction conditions provide a favorable choice for the synthesis of a series of fused triazole derivatives.This thesis designed and synthesized fluorescent probes TCM-1 and TCM-2 with benzothiopyrone as the core structure.And the selective recognition of H₂O₂by TCM-1 and TCM-2 were studied.By testing the UV-vis absorption spectrum and fluorescence emission spectrum of H₂O₂,other active oxygen ions,biological thiols and metal ions in a mixed solution of PBS:DMSO（v:v=7:3）,it was found that TCM-1and TCM-2 are paired H₂O₂had a specific recognition function.TCM-1 and TCM-2 were used as fluorescent markers to successfully monitor H₂O₂in A549 cells and live zebrafish.Moreover,TCM-1 and TCM-2 have fast response time（<1 min）,lower detection limit（70-77 n M）and larger Stokes shift（186 nm）to H₂O₂.Therefore,TCM-1 and TCM-2 have potential application value as H₂O₂ sensors.