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A kind of preparation method and product of carbazolyl-containing chalcone
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A technology for carbazolyl chalcone and carbazole-based carbazole is applied in the field of preparing carbazolyl-containing chalcone, can solve the problems of complicated operation, unsuitable purification and the like, achieves simple experimental operation, reduces intermediate processing steps, and saves raw materials. Effect
Active Publication Date: 2020-06-12
SHAANXI UNIV OF SCI & TECH
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[0004] When using the above method to prepare carbazolyl chalcones, it is first necessary to prepare 3-acetyl-9-substituent carbazole, and due to the symmetry of the structure of N-substituent carbazole, the Friedel-Crafts reaction is carried out to generate 3-acetyl -9-substituent carbazole will generate 3,6-diacetyl-9-substituent carbazole at the same time, so the preparation of high-purity 3-acetyl-9-substituent carbazole is cumbersome and not suitable for purification
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[0036] The preparation method of a kind of carbazolyl-containing chalcone of the present invention, first replaces acrylic acid and phosphorus pentachloride to react to generate substituted acryloyl chloride, then adds 1,2-dichloroethane, Lewis acid (AlCl 3 ) and N-substituent carbazole, Friedel-Crafts reaction occurs to prepare carbazolyl chalcone, and its reaction formula is as follows:
[0037]
[0038] The present invention will be described in further detail below in conjunction with specific examples of the present invention, but the embodiments of the present invention are not limited thereto.
Embodiment 1
[0039] Example 1 Preparation of 1-(3-N-methyl-carbazolyl)-3-phenyl-propenone (1):
[0040]
[0041] In the first step, add 0.05mol cinnamic acid and 0.075mol phosphorus pentachloride to the reaction vessel, stir and react at room temperature for 30min;
[0042] In the second step, after cooling the reaction system to 0°C, a mixed solution of 0.06mol N-methylcarbazole and 25mL 1,2-dichloroethane, 0.06mol AlCl 3 Slowly warming up to reflux temperature, TLC monitoring to the end of the reaction;
[0043] In the third step, an appropriate amount of water is added to the reaction system, stirred evenly, and left to separate liquids, the organic phase is washed with saturated sodiumcarbonate, and the solvent is evaporated to dryness to obtain a crude product;
[0044] In the fourth step, the crude product was recrystallized from absolute ethanol to obtain 1-(3-N-methyl-carbazolyl)-3-phenyl-propenone with a yield of 89.8%, m.p.94-96°C.
[0045] The structural characterization d...
Embodiment 2
[0046] Example 2 Preparation of 1-(3-N-methyl-carbazolyl)-3-(p-chlorophenyl)-propenone (2)
[0047]
[0048] In the first step, add 0.05mol 4-chlorophenylacrylic acid and 0.075mol phosphorus pentachloride to the reaction vessel, and stir and react at room temperature for 30 minutes;
[0049] Second step, with embodiment 1 second step;
[0050] The 3rd step, with the 3rd step of embodiment 1;
[0051] In the fourth step, the crude product was recrystallized from absolute ethanol to obtain 1-(3-N-methyl-carbazolyl)-3-(p-chlorophenyl)-propenone with a yield of 82.4%, m.p.105-106°C .
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Abstract
The invention discloses a preparation method of carbazole-containing chalcone. The preparation method comprises the following steps: a formulated amount of substituted acrylic acid (A) and phosphorus pentachloride (B) are added into a reaction vessel, and react at room temperature for 30 minutes; and then a formulated amount of N-substituted group carbazole (C) solution and Lewis acid (D) are added, and the temperature is slowly raised to refluxing temperature until the reaction is completed; an appropriate amount of water is added into a reaction system, and the mixture is stirred uniformly, is subjected to liquid separation by standing, and is washed and dried by evaporation to obtain a crude product; and the crude product is subjected to recrystallization to obtain a pure product, and the yield can reach 80% or more, wherein A: B: C: D is 1 : (1 to 2) : (1.1 to 1.2) : (1.2 to 1.5). The invention also discloses carbazolyl-containing chalcone compounds. The preparation method provided by the invention can be used for preparing the compounds with high efficiency, high yield and high purity. The antibacterial activity of the compounds are also studied, and experiments show that the compounds have good application prospect in the fields of drug intermediates, antibacterial medicaments and the like.
Description
technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method and product for preparing carbazolyl-containing chalcone. Background technique [0002] The existing method for preparing carbazolyl chalcone is generally to use acetyl carbazole and corresponding aldehydes to undergo Knoevenagel condensation reaction to generate carbazolyl chalcone, and its reaction formula is as follows: [0003] [0004] When using the above method to prepare carbazolyl chalcones, it is first necessary to prepare 3-acetyl-9-substituent carbazole, and due to the symmetry of the structure of N-substituent carbazole, the Friedel-Crafts reaction is carried out to generate 3-acetyl -9-substituent carbazole will generate 3,6-diacetyl-9-substituent carbazole at the same time, so the preparation of high-purity 3-acetyl-9-substituent carbazole is relatively cumbersome and not suitable for purification. However, the purity of the 3-acetyl-9-subst...
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