CN116283768A - Preparation method of aryl acridine compound - Google Patents
Preparation method of aryl acridine compound Download PDFInfo
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- CN116283768A CN116283768A CN202310102512.8A CN202310102512A CN116283768A CN 116283768 A CN116283768 A CN 116283768A CN 202310102512 A CN202310102512 A CN 202310102512A CN 116283768 A CN116283768 A CN 116283768A
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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Abstract
The invention discloses a preparation method of aryl acridine compounds, which comprises the following steps of (1) performing coupling reaction on o-fluorobenzonitrile and aniline under the catalysis of alkali to generate 2-anilino-benzonitrile; step (2) aryl phenol reacts with trifluoromethanesulfonic anhydride to generate trifluoromethanesulfonic acid aryl ester; step (3) reacting the aryl triflate generated in step (2) with a pinacol biborate to generate an arylpinacol borate; and (4) catalyzing the 2-anilino-benzonitrile generated in the step (2) and the arylboronic acid pinacol ester generated in the step (3) to generate the aryl acridine compound. The preparation method is environment-friendly, controllable in process, simple and easy to operate, low in cost and suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of an aryl acridine compound.
Background
Acridine is a very important class of nitrogen-containing heterocycles and has been reported in the fields of medicine, biological probes, sensors, pesticides, organic catalysis, and the like. Acridine is a highly symmetrical nitrogen-containing heterocycle, and derivatives thereof have wide application in different fields, and as drug resistance of bacteria and the like increases, acridine drugs are paid attention again. Acridine drugs are now used in the treatment of various diseases caused by viral, bacterial and protozoal infections. On the other hand, scientists have found that acridine can interact with nucleic acids to exert co-anticancer effects, and that in addition to interactions with DNA, acridine can act on different important cellular enzymes, such as telomerase, topoisomerase, cyclin-dependent kinase, polymerase, etc., helping them to exert their effects. Aryl acridine compound is an important acridine compound, and research on a preparation method of the aryl acridine compound has very important value. One of the existing preparation methods of the aryl acridine compounds is to take o-aminoacetophenone and cyclohexanone as raw materials, take precious metal catalyst, trifluoroacetic acid and TBHP as additives, obtain the aryl acridine compounds in oxygen atmosphere, the characteristic of the reaction is that the yield is low, the catalyst is expensive, the catalyst needs to be carried out in oxygen atmosphere, and the reaction is unsafe; the other method is to prepare the aryl acridine compound by taking diphenylamine and aryl formic acid as raw materials under the action of a metal catalyst, zinc chloride, sulfuric acid and the like.
Disclosure of Invention
The invention aims to provide a preparation method of aryl acridine compounds, which overcomes the defects of 1 in the prior art: the catalyst is expensive, the reaction cost is high, and industrialization is difficult to realize. 2: in the preparation process, more raw materials remain, separation and purification are difficult to realize, and purification is difficult. 3, a step of; the process is complex, the reaction is carried out in a closed environment, and the safety is not high.
Detailed Description
In order to solve the technical problems, the technical scheme of the invention is as follows: a preparation method of aryl acridine compounds comprises the following steps:
the o-fluorobenzonitrile and aniline in the step (1) undergo a coupling reaction under the catalysis of alkali to generate 2-anilino-benzonitrile, wherein the molar ratio of the o-fluorobenzonitrile to the aniline to the alkali is as follows: 1:1-1.5: 1 to 1.5.
Reacting the aryl phenol with trifluoromethanesulfonic anhydride to generate trifluoromethanesulfonic acid aryl ester under the action of organic base, wherein the molar ratio of the aryl phenol to the trifluoromethanesulfonic anhydride to the organic base is as follows: 1:1-1.5: 1 to 1.5.
Step (3) is to generate aryl boric acid pinacol ester by utilizing the aryl trifluoro-sulfonate generated in the step (2) and pinacol ester of bisboric acid under the action of 2-dicyclohexylphosphine-2 ',4',6 '-triisopropylbiphenyl, tris (dibenzylideneacetone) dipalladium and potassium acetate, wherein the molar ratio of the aryl trifluoro-sulfonate compound to the pinacol ester of bisboric acid to the 2-dicyclohexylphosphine-2', 4',6' -triisopropylbiphenyl to the tris (dibenzylideneacetone) dipalladium to the potassium acetate is as follows: 1:1-1.2:0.01:0.01:1-1.2.
Step (4) generating an aryl acridine compound by utilizing the 2-anilino-benzonitrile generated in the step (1) and the aryl boric acid pinacol ester generated in the step (3) under the catalysis of palladium acetate, 2' -bipyridine and trifluoroacetic acid, wherein the molar ratio of the 2-anilino-benzonitrile to the aryl boric acid pinacol ester is as follows: 1:1-1.2:0.01:0.02:1-1.2.
Preferably, the specific reaction step of the step (1) is as follows: adding toluene, o-fluorobenzonitrile and aniline into a three-port bottle protected by reflux reaction nitrogen, stirring uniformly, adding alkali, heating and refluxing to 115 ℃ for reacting for 5 hours, stirring the reaction liquid to room temperature, adding water and stirring for 0.5 hour, standing and separating liquid, separating a lower aqueous phase from an upper organic phase, continuously washing the upper organic phase with water for 3 to 4 times, drying with anhydrous sodium sulfate, filtering, concentrating the organic phase under reduced pressure until the organic phase is dry, and obtaining the 2-anilino-benzonitrile.
Preferably, in the step (1), the molar ratio of the o-fluorobenzonitrile, the aniline and the base is: 1:1.2:1.2.
Preferably, the base in the step (1) is cesium carbonate.
Preferably, the specific reaction step of the step (2) is as follows: adding toluene, aryl phenol, trifluoromethanesulfonic anhydride and organic base into a three-neck flask protected by nitrogen, stirring, dissolving and clearing, heating the reaction liquid to 50 ℃ for reaction for 3 hours, cooling the reaction liquid to room temperature, adding water, stirring, standing for liquid separation, fully washing the lower organic phase to be neutral, and concentrating under reduced pressure to be dry to obtain the trifluoromethanesulfonic aryl ester.
Preferably, the aryl phenol in the step (2) is 4-creosote.
Preferably, the organic base in the step (2) is triethylamine.
Preferably, the molar ratio of the aryl phenol, the trifluoromethanesulfonic anhydride and the organic base in the step (2) is as follows: 1:1.05:1.05.
Preferably, the specific reaction step of the step (3) is as follows: adding dioxane into a three-neck flask, adding a trifluoromethanesulfonic acid aromatic ester compound, pinacol ester biborate, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, tris (dibenzylideneacetone) dipalladium and potassium acetate under stirring, heating and raising the temperature to reflux for 16 hours, cooling the reaction liquid to room temperature, adding water, fully stirring, filtering to obtain a solid, continuously washing the obtained solid with water fully to neutrality, and drying in a drying oven to obtain arylboronic acid pinacol ester.
Preferably, in the step (3), the molar ratio of the aryl triflate, the pinacol biborate, the 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, the tris (dibenzylideneacetone) dipalladium and the potassium acetate is as follows: 1:1.05:0.01:0.01:1.2.
Preferably, the specific reaction step of the step (4) is as follows: toluene, 2-anilino-benzonitrile, arylboronic acid pinacol ester, palladium acetate, 2' -bipyridine and trifluoroacetic acid are added into a three-neck flask, the reaction system is heated to reflux reaction for 12 hours, the reaction solution is slowly poured into water, the solution is separated after stirring, the organic phase is fully washed to be neutral by water, and the mixture is concentrated to be dry under reduced pressure to obtain the aryl acridine compound.
Preferably, the molar ratio of 2-anilino-benzonitrile to step (4), arylboronic acid pinacol ester, palladium acetate, 2' -bipyridine, trifluoroacetic acid is: 1:1.1:0.01:0.02:1.1.
Preferably, the preparation method of the aryl acridine compound is prepared by the synthesis method of any one of claims 1 to 12.
Compared with the prior art, the invention has the advantages that:
(1) The raw materials of o-fluoroaniline, aniline and phenol are cheap and easy to obtain, and the raw materials guarantee is provided for preparing the high-purity low-price aryl acridine compound.
(2) The main product conversion rate of the invention reaches 95%, which is beneficial to the subsequent purification.
(3) The invention greatly reduces the cost of the product and provides technical support for preparing high-purity low-price aryl acridine compounds; provides an important synthetic thought for the synthesis of other acridine derivatives.
(4) The invention has high conversion rate, simple post-treatment operation and easy realization of industrial production.
Detailed Description
Example 1
A preparation method of aryl acridine compounds comprises the following steps:
the reaction equation of step (1) is as follows:
the specific reaction steps of the step (1) are as follows: 150ml of toluene, 12.1g (0.1 mol) of o-fluorobenzonitrile and 11.18g (0.12 mol) of aniline are added into a 250ml three-port bottle protected by reflux reaction nitrogen, after uniform stirring, 39.1g (0.12 mol) of cesium carbonate is added, the temperature is raised and refluxed to 115 ℃ for reaction for 5 hours, then the reaction liquid is stirred to room temperature, water is added and stirred for 0.5 hour, then the mixture is left to stand for separating, a lower aqueous phase and an upper organic phase are separated, the mixture is continuously washed for 3 to 4 times by water, and then dried by anhydrous sodium sulfate, suction filtration and reduced pressure concentration are carried out until the organic phase is dry, thus obtaining 18.45g of 2-anilino-benzonitrile, LC is more than 98%, and the yield is 95% (calculated by o-fluorobenzonitrile).
The reaction equation of step (2) is as follows:
the specific reaction steps of the step (2) are as follows: to a 250ml three-necked flask protected by nitrogen gas, 150ml of toluene, 10.8g (0.1 mol) of 4-toluene phenol, 29.6g (0.105 mol) of trifluoromethanesulfonic anhydride and 10.6g (0.105 mol) of triethylamine are added, the mixture is stirred, dissolved and cleared, the reaction solution is heated to 50 ℃ for reaction for 3 hours, the reaction solution is cooled to room temperature, water is added, the mixture is stirred and then left to stand for liquid separation, the lower organic phase is sufficiently washed to be neutral, and the mixture is concentrated to be dry under reduced pressure to obtain 21.5g of trifluoromethanesulfonic aryl ester, the LC is greater than 97%, and the yield is 89.5% (calculated by 4-methylphenol).
The reaction equation of step (3) is as follows:
the specific reaction steps of the step (3) are as follows: into a 250ml three-neck flask, 100ml dioxane was added, 24g (0.1 mol) of an aryl triflate compound, 26.7g (0.105 mol) of pinacol biborate, 0.47g (0.001 mol) of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, 0.91g (0.001 mol) of tris (dibenzylideneacetone) dipalladium and 19.6g (0.2 mol) of potassium acetate were added under stirring, the reaction solution was heated to reflux for 16 hours, cooled to room temperature, added with water, stirred sufficiently, filtered by suction to obtain a solid, the obtained solid was further washed with water sufficiently to neutrality, and dried in an oven to obtain 19.6g of an aryl pinacol borate with a LC >98% yield of 90% (based on the aryl triflate).
The reaction equation of step (4) is as follows:
the specific reaction steps of the step (4) are as follows: into a 250ml three-necked flask, 100ml of toluene, 19.4g (0.1 mol) of 2-anilino-benzonitrile, 24.0g (0.11 mol) of arylboronic acid pinacol ester, 0.17g (0.001 mol) of palladium acetate, 0.31g (0.002 mol) of 2,2' -bipyridine and 12.5g (0.11 mol) of trifluoroacetic acid were added, the reaction system was heated to reflux and reacted for 12 hours, the reaction solution was slowly poured into water, the solution was separated after stirring, the organic phase was sufficiently washed with water to neutrality, and the mixture was concentrated under reduced pressure until the mixture was dried to obtain 24.2g of an arylacridine compound, LC >99%, and the yield was 90% (based on 2-anilino-benzonitrile).
Elemental analysis (C20H 15N): theoretical value C:89.19%, H:5.61%, N:5.20%; measured value C:89.14%, H:5.58%, N:5.28%.
Example 2
A preparation method of aryl acridine compounds comprises the following steps:
the reaction equation of step (1) is as follows:
the specific reaction steps of the step (1) are as follows: 3L of toluene, 242g (2 mol) of o-fluorobenzonitrile and 224g (2.4 mol) of aniline are added into a 5L three-necked flask protected by reflux reaction nitrogen, after uniform stirring, 782g (2.4 mol) of cesium carbonate is added, the temperature is raised and refluxed to 115 ℃ for reaction for 5 hours, then the reaction solution is stirred and cooled to room temperature, water is added and stirred for 0.5 hour, the mixture is stood and separated, a lower aqueous phase and an upper organic phase are separated, the mixture is continuously washed for 3 to 4 times by water, and then dried by anhydrous sodium sulfate, filtered by suction, and the organic phase is concentrated to dryness under reduced pressure to obtain 369g of 2-anilinobenzonitrile, wherein the LC is more than 98%, and the yield is 95 percent (calculated by o-fluorobenzonitrile).
The reaction equation of step (2) is as follows:
the specific reaction steps of the step (2) are as follows: to a nitrogen-protected 5L three-necked flask, 2.5L of toluene, 216g (2 mol) of 4-toluene phenol, 592g (2.1 mol) of trifluoromethanesulfonic anhydride and 212g (2.1 mol) of triethylamine are added, stirring, dissolving and clearing are carried out, the reaction solution is heated to 50 ℃ for reaction for 3 hours, the reaction solution is cooled to room temperature, water is added, the reaction solution is stirred, then the reaction solution is left to stand and separated, the lower organic phase is sufficiently washed to be neutral, and the reaction solution is concentrated to be dry under reduced pressure to obtain 430g of trifluoromethanesulfonic acid aryl ester, LC is more than 97%, and the yield is 89.5% (calculated by 4-methylphenol).
The reaction equation of step (3) is as follows:
the specific reaction steps of the step (3) are as follows: to a 5L three-necked flask, 2L of dioxane, 480g (2 mol) of an aryl triflate compound, 534g (2.1 mol) of pinacol biborate, 9.4g (0.02 mol) of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, 18.2g (0.02 mol) of tris (dibenzylideneacetone) dipalladium and 392g (4 mol) of potassium acetate were added under stirring, the reaction solution was cooled to room temperature after heating to reflux reaction for 16h, water was added, after sufficient stirring, a solid was obtained after suction filtration, and the obtained solid was further washed with water until neutral, and dried in an oven to obtain pinacol arylborate (392 g, LC > 98%) in a yield of 90% (based on aryl triflate).
The reaction equation of step (4) is as follows:
the specific reaction steps of the step (4) are as follows: to a 5L three-necked flask, 2L toluene, 388g (2 mol) of 2-anilino-benzonitrile, 480g (2.2 mol) of arylboronic acid pinacol ester, 3.4g (0.02 mol) of palladium acetate, 6.2g (0.04 mol) of 2,2' -bipyridine and 250g (2.2 mol) of trifluoroacetic acid were added, the reaction system was heated to reflux for 12 hours, the reaction solution was slowly poured into water, the solution was separated after stirring, the organic phase was sufficiently washed with water to neutrality, and the mixture was concentrated under reduced pressure to dryness to obtain 284 g of arylacridine compound, LC >99% and yield 90% (based on 2-anilino-benzonitrile).
Elemental analysis (C20H 15N): theoretical value C:89.19%, H:5.61%, N:5.20%; measured value C:89.16%, H:5.59%, N:5.25%.
Claims (9)
1. The preparation method of the aryl acridine compound is characterized by comprising the following steps of:
the o-fluorobenzonitrile and aniline in the step (1) undergo a coupling reaction under the catalysis of alkali to generate 2-anilino-benzonitrile, wherein the molar ratio of the o-fluorobenzonitrile to the aniline to the alkali is as follows: 1:1-1.5: 1 to 1.5;
reacting the aryl phenol with trifluoromethanesulfonic anhydride to generate trifluoromethanesulfonic acid aryl ester under the action of organic base, wherein the molar ratio of the aryl phenol to the trifluoromethanesulfonic anhydride to the organic base is as follows: 1:1-1.5: 1 to 1.5;
step (3) is to generate aryl boric acid pinacol ester by utilizing the aryl trifluoro-sulfonate generated in the step (2) and pinacol ester of bisboric acid under the action of 2-dicyclohexylphosphine-2 ',4',6 '-triisopropylbiphenyl, tris (dibenzylideneacetone) dipalladium and potassium acetate, wherein the molar ratio of the aryl trifluoro-sulfonate compound to the pinacol ester of bisboric acid to the 2-dicyclohexylphosphine-2', 4',6' -triisopropylbiphenyl to the tris (dibenzylideneacetone) dipalladium to the potassium acetate is as follows: 1:1-1.2:0.01:0.01:1-1.2;
step (4) generating an aryl acridine compound by utilizing the 2-anilino-benzonitrile generated in the step (1) and the aryl boric acid pinacol ester generated in the step (3) under the catalysis of palladium acetate, 2' -bipyridine and trifluoroacetic acid, wherein the molar ratio of the 2-anilino-benzonitrile to the aryl boric acid pinacol ester is as follows: 1:1-1.2:0.01:0.02:1-1.2.
2. The method for preparing the aryl acridine compound according to claim 1, wherein the specific reaction step of the step (1) is as follows: adding toluene, o-fluorobenzonitrile and aniline into a three-port bottle protected by reflux reaction nitrogen, stirring uniformly, adding alkali, heating and refluxing to 115 ℃ for reacting for 5 hours, stirring the reaction liquid to room temperature, adding water and stirring for 0.5 hour, standing and separating liquid, separating a lower aqueous phase from an upper organic phase, continuously washing the upper organic phase with water for 3 to 4 times, drying with anhydrous sodium sulfate, filtering, concentrating the organic phase under reduced pressure until the organic phase is dry, and obtaining the 2-anilino-benzonitrile.
3. The method for preparing the aryl acridine compound according to claim 2, wherein the method comprises the following steps: the alkali in the step (1) is any one of sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, triethylamine and pyridine.
4. The method for preparing the aryl acridine compound according to claim 1, wherein the specific reaction step of the step (2) is as follows: adding toluene, aryl phenol, trifluoromethanesulfonic anhydride and organic base into a three-neck flask protected by nitrogen, stirring, dissolving and clearing, heating the reaction liquid to 50 ℃ for reaction for 3 hours, cooling the reaction liquid to room temperature, adding water, stirring, standing for liquid separation, fully washing the lower organic phase to be neutral, and concentrating under reduced pressure to be dry to obtain the trifluoromethanesulfonic aryl ester.
5. The method for preparing the aryl acridine compound according to claim 5, wherein the method comprises the following steps: the aryl phenol in the step (2) is any one of phenol, 4-creosote, 4-methoxyphenol and 3, 5-dimethoxy phenol.
6. The method for preparing the aryl acridine compound according to claim 5, wherein the method comprises the following steps: the organic base in the step (2) is any one of triethylamine, pyridine, diisopropylamine and piperidine.
7. The method for preparing the aryl acridine compound according to claim 1, wherein the specific reaction step of the step (3) is as follows: adding dioxane into a three-neck flask, adding a trifluoromethanesulfonic acid aromatic ester compound, pinacol ester biborate, 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, tris (dibenzylideneacetone) dipalladium and potassium acetate under stirring, heating and raising the temperature to reflux for 16 hours, cooling the reaction liquid to room temperature, adding water, fully stirring, filtering to obtain a solid, continuously washing the obtained solid with water fully to neutrality, and drying in a drying oven to obtain arylboronic acid pinacol ester.
8. The method for preparing the aryl acridine compound according to claim 1, wherein the specific reaction step of the step (4) is as follows: toluene, 2-anilino-benzonitrile, arylboronic acid pinacol ester, palladium acetate, 2' -bipyridine and trifluoroacetic acid are added into a three-neck flask, the reaction system is heated to reflux reaction for 12 hours, the reaction solution is slowly poured into water, the solution is separated after stirring, the organic phase is fully washed to be neutral by water, and the mixture is concentrated to be dry under reduced pressure to obtain the aryl acridine compound.
9. A preparation method of aryl acridine compounds is characterized in that: the preparation method of the aryl acridine compound is prepared by the synthesis method of any one of claims 1 to 12.
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