A kind of preparation method of polysubstituted oxazole-2(3h)-one compounds
A ketone compound, multi-substitution technology, applied in the field of preparation of multi-substituted oxazol-2-one compounds, can solve problems such as limiting the scope of application
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[0034] The invention provides a method for preparing a polysubstituted oxazol-2(3H)-one compound, comprising: reacting the acrylamide compound represented by the formula (I) with a hypervalent iodine reagent in the presence of an auxiliary, The polysubstituted oxazol-2(3H)-one compound represented by formula (II) is obtained;
[0035]
[0036] where -R 1 , -R 2 with -R 4 each independently -A, -Ar or -Het; -R 3 for -A;
[0037] The -A is a C1-C30 chain alkyl group, a C1-C30 substituted chain alkyl group or a C3-C7 cycloalkyl group, preferably a C1-C20 chain alkyl group, a C1-C20 substituted chain alkyl group Alkyl or C3-C7 cycloalkyl, more preferably C1-C10 chain alkyl, C1-C10 substituted chain alkyl or C3-C7 cycloalkyl, more preferably C1-C5 chain Alkyl, C1-C5 substituted chain alkyl or C3-C7 cycloalkyl, most preferably C1-C3 chain alkyl, C1-C3 substituted chain alkyl or C3-C7 cycloalkyl .
[0038] The number of substituents in the C1-C30 substituted chain alkyl gro...
Embodiment 1
[0056] Synthesis of 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one
[0057] At room temperature, 1.5 mmol of PIFA, 1.0 mmol of TFA and 40.0 mL of dichloromethane were added to a 50 mL round-bottomed flask and mixed well, and then 1.0 mmol of N-(4′-methylphenyl)- 2-Acetyl-3-methylamino-2-butenamide, react at room temperature for 0.5 hours. After the reaction, the reaction solution was poured into 50.0 mL of saturated NaCl aqueous solution, and then extracted three times with 20.0 mL of dichloromethane. The organic phases were combined, dried by adding 3.0 g of anhydrous sodium sulfate, filtered to remove the solid, and then the organic solvent was removed. , the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=5:1) to obtain 3-(4′-methylphenyl)-4-acetyl-5-methyl-oxazole-2( 3H)-ketone in 65% yield, >99% purity.
[0058] The 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one obtained in Example 1 was analyzed by nuclear magnet...
Embodiment 2
[0062] Synthesis of 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one
[0063] At room temperature, 2.0 mmol of PhIO, 3.0 mmol of TFA and 20.0 mL of 1,2-dichloroethane were added to a 50 mL round-bottomed flask and mixed well, and then 1.0 mmol of N-(4′-methylmethane was added) phenyl)-2-acetyl-3-methylamino-2-butenamide, and reacted at room temperature for 4.0 hours. After the reaction, the reaction solution was poured into 50.0 mL of saturated NaCl aqueous solution, and then extracted three times with 20.0 mL of dichloromethane. The organic phases were combined, dried by adding 3.0 g of anhydrous sodium sulfate, filtered to remove the solid, and then the organic solvent was removed. , the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=5:1) to obtain 3-(4′-methylphenyl)-4-acetyl-5-methyl-oxazole-2( 3H)-ketone in 55% yield, >99% purity.
[0064] The 3-(4'-methylphenyl)-4-acetyl-5-methyl-oxazol-2(3H)-one obtained in Example 2 was...
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