A method for synthesizing chromone derivatives by phio-mediated dehydrogenation reaction
A technology of derivatives and chromones, which is applied in the field of synthesis of chromone derivatives, achieves the effects of high yield, simple operation and easy availability of raw materials
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Embodiment 1
[0030] Preparation of ethyl 4-oxo-2-phenyl-4H-chromone-3-carboxylate (I-a)
[0031]
[0032] The compound ethyl 4-oxo-2-phenylchroman-3-carboxylate II-a (1 mmol) was dissolved in DMF (4 mL) with stirring at ambient temperature. PhIO (2 mmol) was added to the above DMF solution. The resulting mixture was stirred at ambient temperature for about 10 minutes. After checking that the reaction was complete, water was added to the solvent and extracted with ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the crude product was purified by flash column chromatography (ethyl acetate / petroleum ether=15 / 85) to obtain 282 mg of the desired white solid (I-a), with a yield of 89%. The melting point is 81-82°C. 1 H NMR (600MHz, CDCl 3 )δ8.27(dd, J=8.0,1.6Hz,1H),7.76(d,J=6.6Hz,2H),7.73(td,J=8.4,1.8Hz,1H).7.56(t,J=7.2 Hz,1H),7.54-7.50(m,3H),7.45(t,J=7.2Hz,1H),4.28(q,J=7.2Hz,2H)1.17(t,J=7.2Hz,...
Embodiment 2
[0049]Preparation of ethyl 2-(2-furyl)-4-oxo-4H-chromone-3-carboxylate (I-b)
[0050]
[0051] With stirring at ambient temperature, compound ethyl 2-(2-furyl)-4-oxochroman-3-carboxylate II-b (1 mmol) was dissolved in DMF (4 mL). PhIO (2 mmol) was added to the above DMF solution. The resulting mixture was stirred at ambient temperature for about 10 minutes. After checking that the reaction was complete, water was added to the solvent and extracted with ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the crude product was purified by flash column chromatography (ethyl acetate / petroleum ether=15 / 85) to obtain the desired white solid (I-b) 240 mg, yield 78%. The melting point is 88-90°C. 1 H NMR (600MHz, CDCl 3 )δ8.22(dd, J=7.8,1.6Hz,1H),7.72–7.67(m,1H),7.63(d,J=1.0Hz,1H),7.50(d,J=8.4Hz,1H), 7.45–7.38(m,1H),7.23(d,J=3.4Hz,1H),6.64(dd,J=3.4,1.8Hz,1H),4.48(q,J=7.2Hz,2H),1.40(t ,...
Embodiment 3
[0063] Preparation of 3-acetyl-2-phenyl-4H-chromanone-4-one (I-c)
[0064]
[0065] With stirring at ambient temperature, compound 3-acetyl-2-chroman-4-one II-c (1 mmol) was dissolved in DMF (4 mL). PhIO (2 mmol) was added to the above DMF solution. The resulting mixture was stirred at ambient temperature for about 10 minutes. After checking that the reaction was complete, water was added to the solvent and extracted with ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the crude product was purified by flash column chromatography (ethyl acetate / petroleum ether=15 / 85) to obtain the desired colorless oil (I-c) 193 mg, yield 73%. 1 HNMR (600MHz, CDCl 3 )δ8.25(dd,J=8.0,1.4Hz,1H),7.76–7.70(m,1H),7.69–7.64(m,2H),7.57-7.49(m,4H),7.46(t,J= 7.6Hz,1H),2.46(s,3H). 13 C NMR (150MHz, CDCl 3 )δ200.5, 175.9, 162.5, 155.9, 134.4, 131.9, 131.6, 128.9, 128.6, 126.0, 125.7, 124.9, 123.5, 118....
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