CN110156676B - 3, 4-dihydroquinoline-2 (1H) -ketone derivative and preparation method and application thereof - Google Patents
3, 4-dihydroquinoline-2 (1H) -ketone derivative and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses 3, 4-dihydroquinoline-2 (1)H) -ketone derivatives, their preparation and use, characterized in that: in an organic solvent, reacting aniline derivatives with oxalyl chloride, and adding a certain amount of water into a reaction system for hydrolysis; then, a certain amount of olefin derivative, photosensitizer and alkali are added into the reaction system, and the obtained reaction solution is cooled to 60 ℃ at room temperatureoC, irradiating the reaction mixture by visible light till the reaction is complete, extracting, drying, concentrating under reduced pressure, and performing column chromatography separation or recrystallization on the reaction mixture to obtain the high-purity 3, 4-dihydroquinoline-2 (1)H) The invention starts from simple and easily-obtained raw materials for the first time, and realizes a three-step one-pot method strategy to quickly obtain the 3, 4-dihydroquinoline-2 (1) with a novel structureH) The ketone compound has new characteristics and biological activity proved by experiments, and particularly has obvious effect on treating senile dementia.
Description
The technical field is as follows:
the invention belongs to the technical field of organic synthesis, and particularly relates to a 3, 4-dihydroquinoline-2 (1H) -ketone derivative, and a preparation method and application thereof.
Technical background:
quinolinone compounds are important heterocyclic compounds and are core structures in natural products and pharmaceutically active molecules. The 3, 4-dihydroquinoline-2 (1H) -ketone compound has remarkable biological activity and is one of research hotspots of scientists due to a large amount of application in medicines, and the 3, 4-dihydroquinoline-2 (1H) -ketone compound has good biological activity in the aspects of resisting cancers, resisting platelet aggregation, resisting convulsion, treating HIV, treating cardiovascular diseases, treating malaria, treating osteoporosis and the like. Therefore, the synthesis of the nitrogen-containing heterocyclic ring has important medical value and research significance, and how to efficiently synthesize the nitrogen-containing heterocyclic ring also becomes a topic with practical research value and significance, and is widely concerned by chemists.
In recent years, the following methods have been used for the catalytic synthesis of quinolinone compounds. Under the photocatalysis condition, N-hydroxyphthalimide oxalate is used as a raw material to react with electron-deficient olefin to generate a 3, 4-dihydroquinoline-2 (1H) -ketone compound (shown as formula 1, Petersen, W.F.; Taylor, R.J.K.; Donald, J.R.org.Lett.2017, 19,874.). N-hydroxyphthalimide is subjected to two-step acylation reaction at low temperature to obtain a substrate oxalate (NHPI ester). NHPI ester can react with electron-deficient olefin at room temperature in the presence of a photosensitizer by taking toluene as a solvent to obtain the 3, 4-dihydroquinoline-2 (1H) -ketone compound. Although the reaction has good substrate universality and can effectively obtain various substituted target products, the preparation process of the substrate is complex and the operation is complex, the reaction is not only required to be carried out under the condition of low temperature, but also the substrate is required to be stored in a dark place, and meanwhile, the reaction atom has poor economy and strong solvent toxicity and is difficult to be applied to industrial production.
The chemical reaction formula is as follows:
another approach has been disclosed in the inventor's prior application 201810009403.0: the method comprises the steps of using the oxamic acid as a raw material, using silver nitrate as a catalyst, using peroxy compounds (such as sodium persulfate, potassium persulfate and the like) as an oxidant, and performing decarboxylation under a heating condition to synthesize the 3, 4-dihydroquinoline-2 (1H) -ketone compound (formula 2, eq 1). Furthermore, the inventors reported that 2 mol% of Ir [ dF (CF) was used as a starting material for oxalic acid3)ppy]2(dtbbpy)PF6As photosensitizer, the method comprises the step of decarboxylation of the oxamic acid and ring closing of olefin at room temperature to obtain the 3, 4-dihydroquinoline-2 (1H) -ketone compound (shown as a formula 2, eq (2), Bai, Q-F; Jin C.; He J. -Y.; Feng, G.Org.Lett.2018,20, 2172-2175). The chemical reaction formula related to the technical scheme is as follows:
in the above process, although the preparation of the starting material, oxamic acid, is relatively simple and the atom economy of the reaction is improved compared to the first method, the following problems still remain:
1. the reaction steps are multiple, and the time is long: the raw material, namely the oxamic acid, also needs to be obtained through three steps of aniline acylation reaction, methyl ester hydrolysis reaction and acidification reaction, so that the preparation is complicated, the atom economy is poor, the cost is high, and the reaction time is long.
2. Due to the limitation of the starting materials, 3, 4-dihydroquinoline-2 (1H) -ketone derivatives with various structures cannot be rapidly obtained, and the like.
The invention content is as follows:
in order to solve the problems of the above methods, the first aspect of the present invention is to provide a 3, 4-dihydroquinolin-2 (1H) -one derivative having the formula V-a, V-b, V-c:
a second aspect of the present invention is directed to a process for the preparation of 3, 4-dihydroquinolin-2 (1H) -one derivatives, comprising the steps of: adding magnetons, anhydrous dichloromethane and a certain amount of oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl p-methylaniline into the anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, adding purified water, a photosensitizer and a certain amount of alkali into the reaction tube in sequence, sealing the reaction tube, bubbling for 5 minutes by nitrogen, injecting 1-penten-3-one into the reaction tube, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
a preparation method of 3, 4-dihydroquinoline-2 (1H) -ketone derivatives is characterized by comprising the following steps: adding magnetons, anhydrous dichloromethane and oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl p-methylaniline into the anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, adding purified water, a photosensitizer, a certain amount of alkali and phenyl vinyl sulfone into the reaction tube in sequence, sealing the reaction tube, bubbling nitrogen for 5 minutes, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
a preparation method of 3, 4-dihydroquinoline-2 (1H) -ketone derivatives is characterized by comprising the following steps: adding magnetons, anhydrous dichloromethane and oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl aniline into anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, sequentially adding purified water, a photosensitizer and a certain amount of alkali into the reaction tube, sealing the reaction tube, bubbling for 5 minutes by nitrogen, injecting ethyl acrylate into the reaction tube, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
further settings are as follows:
the molar weight of the oxalyl chloride is 5-20 times of that of the substituted aniline.
The photosensitizer is Ir [ dF (CF)3)ppy]2(dtbbpy)(PF6)、Ir[dF(CF3)ppy]2(bpy)(PF6)、 Ru(ppy)3Cl2Rhodamine B or Eosin Y, wherein the molar weight of the photosensitizer is 1-5% of that of the substituted aniline.
The alkali is one or more of potassium carbonate, potassium phosphate, potassium hydrogen phosphate, dipotassium hydrogen phosphate, cesium carbonate, sodium carbonate, lithium carbonate and sodium hydroxide, and the molar weight of the alkali is 2-10 times of that of the substituted aniline.
The reaction temperature under blue light is room temperature to 60 ℃.
The third aspect of the invention is to provide the application of the 3, 4-dihydroquinoline-2 (1H) -ketone derivative in preparing the acetylcholinesterase inhibiting medicine.
The invention has the following beneficial effects:
(1) the invention prepares a brand-new 3, 4-dihydroquinoline-2 (1H) -ketone derivative, and through structure confirmation and performance detection, the novel compound has a remarkable effect on inhibiting acetylcholinesterase and can be used for preparing medicaments for treating diseases such as senile dementia and the like.
(2) The synthesis method realizes the synthesis of the 3, 4-dihydroquinoline-2 (1H) -ketone derivative by a three-step one-pot method through the selection of the substituted aniline and the olefin as raw materials, the selection and the dosage of the photosensitive catalyst and the control of reaction conditions, does not need intermediate purification, has good reaction atom economy, takes water as a reaction reagent and a cosolvent, and meets the requirement of green chemistry.
The present invention will be further described with reference to the following detailed description.
The specific implementation mode is as follows:
example 1: preparation of a Compound of formula V-a
The preparation method comprises the following steps:
adding magneton, anhydrous dichloromethane (2.0mL) and a certain amount of oxalyl chloride (0.6mmol-3mmol) into a 20mL reaction tube in turn, stirring at room temperature, dissolving N-benzyl p-methylaniline (0.3mmol) in 2mL anhydrous dichloromethane, rapidly injecting into the reaction tube, detecting aniline by TLC until complete reaction, reacting for about 1 hour, adding purified water (2.0mL) and photosensitizer Ir [ dF (CF) into the reaction tube in turn3)ppy]2(dtbbpy)(PF6)(2mol％)，K2CO3(1.5mmol), the reaction tube was sealed, nitrogen was bubbled for 5 minutes, and 1-penten-3-one (0.9mmol) was injected into the reaction tube and reacted for 36 hours under 36W LED blue light. Extracting the reaction liquid with ethyl acetate (40mL) and water (10mL), reserving an organic phase, washing the organic phase with saturated saline solution, drying the organic phase with anhydrous sodium sulfate, concentrating the organic phase under reduced pressure, separating the organic phase by column chromatography to obtain a corresponding target product, and drying the target product by a vacuum oil pump to obtain the product.
The structure of the compound is confirmed:
v-a Structure, H1-NMR and13the C NMR data are as follows:
1H NMR(400MHz,CDCl3)ppm 7.31-7.28(m,2H),7.24-7.20(m,3H),7.10(d,J＝1.6Hz,1H),6.98(d,J＝8.0,1.2Hz,1H),6.80(d,J＝8.4Hz,1H),5.21and 5.11(AB q,J＝16.0,16.0Hz,2H),3.85(dd,J＝6.0,2.8Hz,1H),3.16(dd,J＝16.0,2.8 Hz,1H),2.84(dd,J＝16.0,6.0Hz,1H),2.55-2.49(m,2H),2.31(s,3H),1.01(t, J＝7.2Hz,3H).
13C NMR(100MHz,CDCl3)ppm 208.2,168.8,137.0,136.9,132.7,129.5,129.2,128.6,127.0,126.7,123.1,116.2,49.1,45.5,33.4,33.3,20.5,7.6。
examples 2 to 4:
the preparation method of example 1 was followed to adjust the dosage of oxalyl chloride to obtain examples 2-4, and the effect of the dosage of oxalyl chloride on the yield was examined, and the statistical results are shown in Table 1.
Table 1: effect of different amounts of oxalyl chloride on yield
As shown in Table 1, the amount of oxalyl chloride had a large effect on the yield, and the reaction yield was significantly improved as the amount of oxalyl chloride was increased. When the ratio of N-methylaniline: the reaction yield can be 57% at 1:10 oxalyl chloride.
Examples 5 to 7: effect of different photosensitizers on yield
The preparation method comprises the following steps:
adding magneton, anhydrous dichloromethane (2.0mL) and oxalyl chloride (3.0mmol) into a 20mL reaction tube in turn, stirring at room temperature, dissolving N-benzyl-p-methylaniline (0.3mmol) in 2mL anhydrous dichloromethane, rapidly injecting into the reaction tube, detecting aniline by TLC until complete reaction, reacting for about 1 hour, adding purified water (2.0mL), different photosensitizers (2 mol%), K into the reaction tube in turn2CO3(1.5mmol), the reaction tube was sealed, nitrogen was bubbled for 5 minutes, and 1-penten-3-one (0.9mmol) was injected into the reaction tube and reacted for 36 hours under 36W LED blue light. Extracting the reaction liquid with ethyl acetate (40mL) and water (10mL), reserving an organic phase, washing the organic phase with saturated saline solution, drying the organic phase with anhydrous sodium sulfate, concentrating the organic phase under reduced pressure, separating the organic phase by column chromatography to obtain a corresponding target product, and drying the target product by a vacuum oil pump to obtain the product.
According to the above preparation method, different photosensitizers were used, and the effect of different photosensitizers on the yield was examined, and the statistical results are shown in table 2.
Table 2: effect of different photosensitizers on yield
| Examples | 4 | 5 | 6 | 7 |
| Photosensitizers | Ir[dF(CF3)ppy]2(dtbbpy)(PF6) | Ir(ppy)3 | Ru(ppy)3Cl2 | Eosin Y |
| Yield of | 57 | 11 | 17 | 0 |
As shown in Table 2, different photosensitizers had a greater effect on yield, as measured by Ir (ppy)3、Ru(ppy)3Cl2The yield of the catalyst is low; the yield of photosensitizer with Eosin Y is 0%; with Ir [ dF (CF)3)ppy]2(dtbbpy)(PF6) The catalyst has the highest reaction yield of 57%.
Example 8: preparation of the Compound represented by V-b
The preparation method comprises the following steps:
adding magneton, anhydrous dichloromethane (2.0mL) and oxalyl chloride (3.0mmol) into a 20mL reaction tube in turn, stirring at room temperature, dissolving N-benzyl-p-methylaniline (0.3mmol) in 2mL anhydrous dichloromethane, rapidly injecting into the reaction tube, detecting aniline by TLC until complete reaction, reacting for about 1 hour, adding purified water (2.0mL) and photosensitizer Ir [ dF (CF) into the reaction tube in turn3)ppy]2(dtbbpy)(PF6) (2 mol%), a quantity of base, phenyl vinyl sulfone (0.9mmol), sealing the reaction tube, bubbling nitrogen for 5 minutes, and reacting under 36W LED blue light for 36 hours. The reaction mixture was extracted with ethyl acetate (40mL) and water (10mL), the organic phase was retained, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatographySeparating to obtain corresponding target products, and pumping the target products through a vacuum oil pump to obtain the product with the yield of 43 percent.
The structure of the compound is confirmed:
1H NMR(400MHz,CDCl3)ppm 7.70-7.64(m,3H),7.53-7.49(m,2H),7.32-7.28 (m,2H),7.25-7.24(m,1H),7.17-7.13(m,3H),7.04(dd,J＝8.4,1.6Hz,1H),6.63 (d,J＝8.4Hz,1H),5.10and 4.02(AB q,J＝16.4,16.4Hz,2H),4.36(d,J＝7.2 Hz,1H),3.48(d,J＝17.6,Hz,1H),3.18(dd,J＝17.6,7.6Hz,1H),2.30(s,3H).
13C NMR(100MHz,CDCl3)ppm 165.3,138.2,136.4,136.0,134.2,132.9,132.2,131.2,129.6,128.8,128.7,127.1,126.1,115.9,115.7,63.1,46.5,31.9,20.4。
example 9: preparation of Compounds of formula V-c
The preparation method comprises the following steps:
adding magneton, anhydrous dichloromethane (2.0mL) and oxalyl chloride (3.0mmol) into a 20mL reaction tube in sequence, stirring at room temperature, dissolving N-benzylaniline (0.3mmol) in 2mL anhydrous dichloromethane, rapidly injecting into the reaction tube, detecting aniline by TLC until complete reaction, reacting for about 1 hour, adding purified water (2.0mL) and photosensitizer Ir [ dF (CF) into the reaction tube in sequence3)ppy]2(dtbbpy)(PF6)(2mol％)，K2CO3(1.5mmol), the reaction tube was sealed, nitrogen was bubbled for 5 minutes, ethyl acrylate (0.9mmol) was injected into the reaction tube, and the reaction was carried out for 36 hours under 36W LED blue light. Extracting the reaction liquid by using ethyl acetate (40mL) and water (10mL), reserving an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, concentrating the organic phase under reduced pressure, carrying out column chromatography separation to obtain a corresponding target product, and carrying out vacuum oil pump drying to obtain the product, wherein the yield is 52%.
The structure of the compound is confirmed:
1H NMR(400MHz,CDCl3)ppm 7.34-7.29(m,3H),7.26-7.23(m,3H),7.19(ddd, J＝8.0,7.6,1.6Hz,1H),7.03(ddd,J＝3.6,3.6,0.8Hz,1H),6.92(d,J＝8.0 Hz,1H),5.22(s,2H),4.22-4.16(m,2H),3.94(dd,J＝6.0,4.0Hz,1H),3.18(dd, J＝16.4,4.4Hz,1H),2.96(dd,J＝16.4,6.4Hz,1H),1.25(t,J＝7.2Hz,3H).
13C NMR(100MHz,CDCl3)ppm 171.6,168.3,139.4,136.8,128.8,128.7,127.1,126.5,123.1,122.7,116.0,61.5,45.9,42.4,33.8,14.1。
the application example is as follows:
the compounds V-a, V-b, V-c prepared as described above were tested for their inhibition of acetylcholinesterase (AChE) activity.
The test method is as follows:
to each well of the 96-well plate, 40. mu.L of phosphate buffer (pH 8.0) was added, and then to the corresponding well, 0.39, 0.78, 1.56, 3.125, 6.25, 12.5, 25, 50 and 100. mu.M of 10. mu.L of test compound solution or blank was added, followed by addition of 10. mu.L of AChE, and shaking incubation at 37 ℃ for 5 min. Adding 20 mu L of DTNB (5, 5-dithiobis (2-nitrobenzoic acid)) solution serving as a color developing agent, placing the mixture in a 37 ℃ shaking table for incubation for 5min, then adding 10 mu L of substrate ATC (thioacetyl choline iodide serving as a substrate) and placing the mixture in a 37 ℃ shaking table for incubation for 3min, measuring the absorbance at 412nm by using an enzyme labeling instrument, setting three repeated holes, and calculating the inhibition rate of the compound to be tested on AChE. The enzyme activity inhibition ratio R is calculated according to the formula 1-1, wherein A0Denotes the absorption value without sample, ASTo add the absorbance of both the sample and the enzyme, ABThe absorbance without enzyme is shown. Determination of the IC of the Compounds from the inhibition curves50The value (the concentration of the inhibitor at which the enzyme activity was inhibited by 50%) was plotted on the abscissa of the sample concentration (. mu.g/mL) and on the ordinate of the inhibition rate of the enzyme activity, and the median Inhibitory Concentration (IC) was calculated50). The results of the experiments are shown in the following table:
TABLE 1,
| Compounds | IC50(μM) | Compounds | IC50(μM) |
| v-a | 121±3 | v-b | 154±5 |
| v-c | 101±5 |
As can be seen from the data in the table above:
the compound prepared by the invention has good inhibition rate on acetylcholinesterase (AChE), can be used for preparing medicines for treating senile dementia and the like, and has good application prospect.
Claims (8)
1. A3, 4-dihydro-2 (1H) -quinolinone compound is characterized in that the structural formula is shown as formulas V-a, V-b and V-c:
2. a process for the preparation of 3, 4-dihydro-2 (1H) -quinolinone compounds as claimed in claim 1, comprising the steps of: adding magnetons, anhydrous dichloromethane and a certain amount of oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl p-methylaniline into the anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, adding purified water, a photosensitizer and a certain amount of alkali into the reaction tube in sequence, sealing the reaction tube, bubbling for 5 minutes by nitrogen, injecting 1-penten-3-one into the reaction tube, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
the photosensitizer is Ir [ dF (CF)3)ppy]2(dtbbpy)(PF6)、Ir[dF(CF3)ppy]2(bpy)(PF6) Or Ru (ppy)3Cl2The molar weight of the photosensitizer is 1-5% of that of the substituted aniline.
3. A process for the preparation of 3, 4-dihydro-2 (1H) -quinolinone compounds as claimed in claim 1, comprising the steps of: adding magnetons, anhydrous dichloromethane and oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl p-methylaniline into the anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, adding purified water, a photosensitizer, a certain amount of alkali and phenyl vinyl sulfone into the reaction tube in sequence, sealing the reaction tube, bubbling nitrogen for 5 minutes, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
the photosensitizer is Ir [ dF (CF)3)ppy]2(dtbbpy)(PF6)、Ir[dF(CF3)ppy]2(bpy)(PF6) Or Ru (ppy)3Cl2The molar weight of the photosensitizer is 1-5% of that of the substituted aniline.
4. A process for the preparation of 3, 4-dihydro-2 (1H) -quinolinone compounds as claimed in claim 1, comprising the steps of: adding magnetons, anhydrous dichloromethane and oxalyl chloride into a reaction tube in sequence, stirring at room temperature, dissolving N-benzyl aniline into anhydrous dichloromethane, quickly injecting into the reaction tube, detecting aniline by TLC (thin layer chromatography) until complete reaction, sequentially adding purified water, a photosensitizer and a certain amount of alkali into the reaction tube, sealing the reaction tube, bubbling for 5 minutes by nitrogen, injecting ethyl acrylate into the reaction tube, and reacting for 36 hours under 36W LED blue light; extracting the reaction liquid by using ethyl acetate and water, retaining an organic phase, washing the organic phase by using saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, carrying out reduced pressure concentration, carrying out column chromatography separation to obtain a corresponding target product, and pumping the target product by using a vacuum oil pump to obtain the product, wherein the structural formula of the product is as follows:
the photosensitizer is Ir [ dF (CF)3)ppy]2(dtbbpy)(PF6)、Ir[dF(CF3)ppy]2(bpy)(PF6) Or Ru (ppy)3Cl2The molar weight of the photosensitizer is 1-5% of that of the substituted aniline.
5. The method for producing 3, 4-dihydro-2 (1H) -quinolinone compounds according to any one of claims 2 to 4, characterized in that: the molar weight of the oxalyl chloride is 5-20 times of that of the substituted aniline.
6. The method for producing 3, 4-dihydro-2 (1H) -quinolinone compounds according to any one of claims 2 to 4, characterized in that: the alkali is one or more of potassium carbonate, potassium phosphate, dipotassium hydrogen phosphate, cesium carbonate, sodium carbonate, lithium carbonate and sodium hydroxide, and the molar weight of the alkali is 2-10 times that of the substituted aniline.
7. The method for producing 3, 4-dihydro-2 (1H) -quinolinone compounds according to any one of claims 2 to 4, characterized in that: the reaction temperature under blue light is room temperature to 60 ℃.
8. Use of 3, 4-dihydro-2 (1H) -quinolinone compounds as claimed in claim 1 in the preparation of a medicament for inhibiting acetylcholinesterase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201910558987.1A CN110156676B (en) | 2019-06-26 | 2019-06-26 | 3, 4-dihydroquinoline-2 (1H) -ketone derivative and preparation method and application thereof |
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Citations (4)
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| CN102307867A (en) * | 2009-02-06 | 2012-01-04 | 大正制药株式会社 | Dihydroquinolinone derivatives |
| CN106831714A (en) * | 2017-01-23 | 2017-06-13 | 南阳师范学院 | A kind of tetrahydro isoquinoline compound and its production and use |
| CN107987017A (en) * | 2018-01-05 | 2018-05-04 | 绍兴文理学院 | A kind of 3,4-dihydro-2 (1H)-quinolinones compound and preparation method and application |
| CN108863846A (en) * | 2017-05-09 | 2018-11-23 | 武汉先路医药科技股份有限公司 | A kind of preparation method of lodoxamide tromethamine intermediate |
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| CN102307867A (en) * | 2009-02-06 | 2012-01-04 | 大正制药株式会社 | Dihydroquinolinone derivatives |
| CN106831714A (en) * | 2017-01-23 | 2017-06-13 | 南阳师范学院 | A kind of tetrahydro isoquinoline compound and its production and use |
| CN108863846A (en) * | 2017-05-09 | 2018-11-23 | 武汉先路医药科技股份有限公司 | A kind of preparation method of lodoxamide tromethamine intermediate |
| CN107987017A (en) * | 2018-01-05 | 2018-05-04 | 绍兴文理学院 | A kind of 3,4-dihydro-2 (1H)-quinolinones compound and preparation method and application |
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| Title |
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| Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1H)‑ones;Qi-Fan Bai et.;《Org. Lett.》;20180404;第20卷;第2172-2175页 * |
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