Substituted 6,8-dimercapto-2-phenyl-4H-chromen-4-one derivative and preparation method and application thereof
A substituent, dimercapto technology, applied in the field of organic synthetic drugs, to achieve high activity and selectivity, mild reaction conditions, and low energy consumption
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Embodiment 1
[0028] This example discloses the first synthetic route for the synthesis of flavone derivatives, and its specific synthetic method is:
[0029] (1) Using 5,7-dihydroxyflavone as the initial raw material, under the conditions of nitric acid and acetic acid, adding elemental iodine to prepare intermediate 1a (5,6-dihydroxy-6,8-diiodo-2-phenyl -4H-chromone);
[0030] (2) Use thiophenolic compounds to carry out coupling reaction with intermediate 1a to generate corresponding target compounds.
[0031] First, the preparation of 5,6-dihydroxy-6,8-diiodo-2-phenyl-4hydro-chromone (intermediate 1a) is carried out:
[0032]
[0033] Synthesis of Compound 1a
[0034] 5,7-dihydroxyflavone (5.08g, 20mmol) and elemental iodine (5.76g, 20mmol) were added to a 250ml single-necked bottle, and the solvent was 20ml of dichloromethane and 20ml of glacial acetic acid, stirring at room temperature, while Add 2 g of concentrated nitric acid into 10 ml of glacial acetic acid, and slowly add it...
Embodiment 2
[0044] Carry out object compound 6,8-bis((3-bromophenyl) thio)-5,7-dihydroxy-2-phenyl-4 hydrogen-chromen-4-one (compound 2) Preparation:
[0045]
[0046] Synthesis of Compound 2
[0047] 3-Bromothiophenol (64ul, 0.5mmol), 1a (127mg, 0.25mmol), 60748-47-2 (2.3mg, 0.0025mmol), 657408-07-6 (2.1mg, 0.005mmol) and cesium carbonate (245mg, 0.75mmol) was added into a 50ml three-neck flask, the solvent was DMF, vacuumized, and replaced with nitrogen three times, reacted at 110 degrees, and stirred overnight. To process the reaction, first use diatomaceous earth to filter out the catalyst, ligand and inorganic salt of the reaction solution to obtain a black filtrate, then distill off the solvent N, N-dimethylformamide under reduced pressure to obtain a tan solid, add dichloromethane , and extracted twice with water, the organic phase was dried with anhydrous magnesium sulfate, filtered, the filtrate was spin-dried, and the residue was purified by column chromatography to obtain a...
Embodiment 3
[0051] Carry out object compound 5,7-dihydroxyl-6,8-bis((2-methoxyphenyl)thio)-2-phenyl-4 hydrogen-chromen-4-one ( Compound 3) Preparation:
[0052]
[0053] Synthesis of Compound 3
[0054] With 2-methoxythiophenol (60ul, 0.5mmol), 1a (127mg, 0.25mmol), 60748-47-2 (2.3mg, 0.0025mmol), 657408-07-6 (2.1mg, 0.005mmol) and Cesium carbonate (245mg, 0.75mmol) was added into a 50ml three-necked flask, the solvent was DMF, vacuumized, and replaced with nitrogen three times, reacted at 110°C, and stirred overnight. To process the reaction, first use diatomaceous earth to filter out the catalyst, ligand and inorganic salt of the reaction solution to obtain a black filtrate, then distill off the solvent N, N-dimethylformamide under reduced pressure to obtain a tan solid, add dichloromethane , and extracted twice with water, the organic phase was dried with anhydrous magnesium sulfate, filtered, the filtrate was spin-dried, and the residue was purified by column chromatography to ob...
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