Research On The Green Synthesis Process Of 2-arylbenzopyrone Derivatives

2-Arylbenzopyrone and its derivatives are important oxygen-containing heterocyclic flavonoids,which are ubiquitous in plants.These compounds have been proved by some research that they have anti-tumor,improved vascular permeability and anti-HIV-1 integrase and other biological activities in pharmacological and clinical treatment.In recent years,they have attracted the attention due to their unique chemical structure,excellent pharmacological and biological activities,and its extensive application in clinical medicine.Therefore,the synthesis of 2-arylbenzopyrone flavonoid compounds have important significance and application prospects.Through literature research,a green synthesis method for 2-arylbenzopyrone flavonoid derivatives was designed and developed:Firstly,the inexpensive and readily available o-hydroxyacetophenone and aryl carbonyl chloride were used as the starting materials to obtain a diarylβ-propanedione compound by a phase transfer catalytic one-pot reaction of an esterification reaction and a rearrangement reaction under alkaline condition and microwave irradiation in the mixed solvent of the aprotic organic solvent and water.Next,a cyclization reaction was carried out under the catalysis of trifluoromethanesulfonic acid and copper chloride to obtain a flavonoid compound2-arylbenzopyrone,and the product yield was over 90%;Finally,a green and efficient method for synthesis of 2-arylbenzopyrone flavonoid derivatives was obtained by optimizing the reaction conditions.The method has good industrial production prospects.Ten 2-arylbenzopyrone flavonoids were synthesized by the optimal route,and chemical structure of the target products were confirmed by high resolution mass spectrometry,infrared spectroscopy,¹H-NMR and ¹³C-NMR.Then on the basis of the experiment,a pilot-scale expansion experiment was carried out,and two batches of 10 kg-level pilot production tasks were completed.