Preparation method of seleno-flavonoid compounds
A technology of chromone compounds and selenoflavones, which is applied in organic chemistry and other fields, can solve the problems of narrow substrate range and achieve the effects of short reaction time, high yield and mild reaction conditions
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[0026] Example 1
[0027] Chromone (0.2 mmol), 1,2-diphenyl diselenide (0.1 mmol), NIS (0.04 mmol), TBHP (0.8 mmol) and DMF (2.0 mL) were added to a 5 mL reaction flask, and stirred at 70°C. TLC tracks the detection reaction. After 7 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. Wash the aqueous layer twice with ethyl acetate, combine all the organic layers, and wash twice with water. The organic layer was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 56.6 mg of the product (CAS number: 1980869-97-3), with a yield of 94%. The process is as follows:
[0028]
[0029] Perform nuclear magnetic resonance analysis on the product prepared in this example:
[0030] 1 H NMR(500MHz, DMSO-d 6 )δ8.61(s,1H), 8.07(dd,J=8.0,1.4Hz, 1H), 7.85(dd,J=11.3,4.3Hz,1H), 7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7.44(...
Example Embodiment
[0031] Example 2
[0032] Chromone (0.2 mmol), 1,2-diphenyl diselenide (0.1 mmol), NIS (0.04 mmol), TBHP (0.8 mmol) and DMSO (2.0 mL) were added to a 5 mL reaction flask, and stirred at 70°C. TLC tracks the detection reaction. After 12 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. Wash the aqueous layer twice with ethyl acetate, combine all the organic layers, and wash twice with water. The organic layer was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 27.1 mg of the product with a yield of 45%. The reaction process is shown in the following formula:
[0033]
[0034] Perform nuclear magnetic resonance analysis on the product prepared in this example:
[0035] 1 H NMR(500MHz, DMSO-d 6 )δ8.61(s,1H), 8.07(dd,J=8.0,1.4Hz, 1H), 7.85(dd,J=11.3,4.3Hz,1H), 7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7.4...
Example Embodiment
[0036] Example 3
[0037] Chromone (0.2 mmol), 1,2-diphenyl diselenide (0.1 mmol), NIS (0.04 mmol), TBHP (0.8 mmol) and DCM (2.0 mL) were added to a 5 mL reaction flask, and stirred at 70°C. TLC tracks the detection reaction. After 12 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, and the organic layer was separated. Wash the aqueous layer twice with ethyl acetate, combine all the organic layers, and wash twice with water. The organic layer was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography (10% ethyl acetate petroleum ether solution) to obtain 12.6 mg of the product with a yield of 21%. The reaction process is shown in the following formula:
[0038]
[0039] Perform nuclear magnetic resonance analysis on the product prepared in this example:
[0040] 1 H NMR(500MHz, DMSO-d 6 )δ8.61(s,1H), 8.07(dd,J=8.0,1.4Hz, 1H), 7.85(dd,J=11.3,4.3Hz,1H), 7.68(dd,J=8.5,0.6Hz,1H ),7.55–7.52 (m,1H),7.47–7.44...
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