Preparation method of 3-arylmercapto flavonoid compound
A technology for arylmercaptoflavonoids and compounds is applied in the field of preparing 3-arylmercaptoflavonoid compounds, and can solve the problems of metal palladium catalyst poisoning, difficulty in preparing flavonoids, and difficulty in preparing raw materials of o-methoxybenzoyl alkyne, etc. The product is easy to obtain, the operation is simple, and the process is simple.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
preparation example Construction
[0022] A preparation method of sulfur-containing flavone derivatives, comprising the steps of: using 1-(2-methoxyaryl)-3-aryl propynone and N -Arylthiobenzamide is the reaction substrate, and the molar ratio range of the two is 1:1~1:1.5. By adding 100-200 mol% of anhydrous ferric chloride or aluminum trichloride as one of the promoters, in one of the reaction solvents of dichloromethane, chloroform or 1,2-dichloroethane, React at a temperature of 25°C for 20 h; the chemical reaction formula is as follows:
[0023]
[0024] The -Ar is phenyl, 4-methylphenyl, 4-ethylphenyl, 4-methoxyphenyl, 2-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4- One of the nitrophenyl,
[0025] The -Ar' is phenyl, 4-methylphenyl, 4-methoxyphenyl, 2-fluorophenyl, 4-chlorophenyl, 2-chlorophenyl, 3-chlorophenyl, 3, One of 5-dichlorophenyl, 3-nitrophenyl,
[0026] After the reaction is completed, after cooling, the reaction solution is filtered to obtain a filtrate; the filtrate is subjected to ro...
specific Embodiment 1
[0027] Specific embodiment one: 47.2 milligrams (0.2mmol) 1-(2-methoxyphenyl)-3-phenylpropynone, 55 milligrams (0.24mmol) N -Phenylthiobenzamide, 66 mg (0.4 mmol) of anhydrous ferric chloride, added to 2 mL of dichloromethane solvent. React at room temperature at 25°C for 20 hours, cool after the reaction, filter, and rotate the filtrate to remove the solvent. The residue is chromatographed on a silica gel column and rinsed with a mixed solution of petroleum ether and ethyl acetate at a volume ratio of 15:1. The effluent was collected according to the actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and the white solid was dried in vacuo to obtain 55.4 mg of 2-phenyl-3-phenylthio-4 H -Chromen-4-one, yield 84%. Yellow soil. 1 H NMR (500 MHz, CDCl 3 ) δ 8.26 (d, J = 7.0 Hz,1H), 7.78 (d, J = 7.5 Hz, 2H), 7.73 (t, J = 7.0 Hz, 1H), 7.54-7.44 (m,5H), 7.21 (d, J = 4.5 Hz,4H), 7.14-7.1...
specific Embodiment 2
[0028] Specific embodiment two: 83.4 milligrams (0.3mmol) 1-(2-methoxyphenyl)-3-(4-methylphenyl) propynyl ketone, 82.4 milligrams (0.36mmol) N-Phenylthiobenzamide, 99 mg (0.6 mmol) of anhydrous ferric chloride, added to 2 mL of dichloromethane solvent. React at room temperature at 25°C for 20 hours, cool after the reaction, filter, and rotate the filtrate to remove the solvent. The residue is chromatographed on a silica gel column and rinsed with a mixed solution of petroleum ether and ethyl acetate at a volume ratio of 15:1. The effluent was collected according to the actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was distilled off by a rotary evaporator, and the white solid was dried in vacuo to obtain 95 mg of 2-(4-methylphenyl)-3-phenylthio-4H- Chromen-4-one, yield 85%. Yellow soil. 1 H NMR (500 MHz, CDCl 3 ) δ 8.26 (d, J = 8.0 Hz, 1H), 7.72-7.70 (m, 3H), 7.52 (d, J = 7.5 Hz, 1H), 7.44 (t, J = 7.0 Hz, 1H), 7.28 (d,...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More