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With thionyl chloride for 0.5h; Heating; |
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With thionyl chloride for 2h; Reflux; |
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With dmap; thionyl chloride In dichloromethane for 2h; Reflux; |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere; |
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With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h; |
General procedure for the synthesis of HY-1a-HY-1f
General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f |
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With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; |
General procedure: To a 0 °C stirring solution of substituted aryloxyacetic acid (4a-f, 5.4mmol) in anhydrous dichloromethane (50 mL) was slowly added oxalyl chloride (8 mmol) dropwise. After the reagent addition was complete, the ice bath was removed and the solution was allowed to stand at room temperature for 1 h. The solvent was removed under vacuum to obtain corresponding acyl chloride 5a-f sufficiently pure to be used directly in the next step of the reaction. To a stirred solution of corresponding 1-(substitutedbenzhydryl)piperazine (9a-d, 8mmol), triethylamine (6.8 mL) in dry acetone (30 mL) was slowly added acyl chloride 5a-f, dissolved in anhydrous acetone (30 mL). The mixture was stirred at room temperature for 16h and filtered off. The filtrate was evaporated and purified by column chromatography with AcOEt/petroleum ether (2/1) to give diphenylmethyl-substituted aryloxy acetylpiperazine analogs 10a-s, yield of33-84%. |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h; |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
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