Study On Synthetic Methodology Of Oxaperylenone Derivatives

The oxaperylenone derivatives is a novel organic heterocyclic compound with naphtho[1,2,3-de]benzopyran-2,7-dione skeleton structure,which has a broad spectrum of cytotoxic activity and optics.Properties,such as marine natural products such as Aspergiolide,dibenzocoumarin,etc.,can be used to synthesize new antitumor drugs,laser dyes,fluorescent whitening agents,fluorescent probes and non-linear optical materials,Therefore,the synthesis of such skeletal structure compounds that have great significance.The synthesis methods of oxaperylenone derivatives were studied.The target compounds with different structure types were successfully synthesized by the optimization of reaction conditions.The reaction mechanism was studied.The structure of the compounds in the drug and fluorescence was studied.Applied research laid the foundation.The specific research contents are as follows:(1)12 kinds of oxaperylenone derivatives were synthesized by using Acetic acid9,10-dioxo-9,10-dihydro-anthracen-1-yl ester as a raw material,potassium carbonate as a base,and different β-ketoester compounds by Knoevenagel condensed ring reaction in dimethyl sulfoxide.The highest yield was up to 85%.All the compounds were characterized by nuclear magnetic resonance(NMR),liquid chromatography-mass spectrometry(LC-MS)/high resolution mass spectrometry(HRMS).The possible reaction mechanism was proposed based on the experimental results.The reaction mechanism was further verified by Density functional theory(DFT)theoretical calculations.(2)Using 1-hydroxyindole as raw material,propylphosphoric anhydride(T3P)as a promoter,triethylamine as a base,reacting with β-ketoester compounds,and investigating reaction temperature,base,solvent and reactants The effects of the amount ratio of the substance on the yield of the product,16 kinds of oxaperylenone derivatives were synthesized by the optimization of conditions,and all the compounds were subjected to nuclear magnetic resonance(NMR),liquid chromatography-mass spectrometry(LC-MS)/high resolution mass spectrometry(HRMS)was characterized by structure;a possible reaction mechanism was proposed by controlled experiments.