CN110698399A - Aryl acridine derivative synthesized by palladium catalysis and preparation method thereof - Google Patents
Aryl acridine derivative synthesized by palladium catalysis and preparation method thereof Download PDFInfo
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- CN110698399A CN110698399A CN201911015072.2A CN201911015072A CN110698399A CN 110698399 A CN110698399 A CN 110698399A CN 201911015072 A CN201911015072 A CN 201911015072A CN 110698399 A CN110698399 A CN 110698399A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
Abstract
The invention discloses an aryl acridine derivative synthesized by palladium catalysis and a preparation method thereof, wherein the aryl acridine derivative is prepared by taking a 2- (arylamino) benzonitrile derivative and aryl boric acid as reactants; the reactant has wide sources, easy preparation, low cost and low toxicity, and is not easy to influence human health. The reaction is carried out in a solvent, and the solvent is water; during reaction, a palladium catalyst, an additive and a ligand are also added into the solvent; the palladium catalyst is any one of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate, and the additive is methanesulfonic acid; the reaction temperature is 90-110 ℃, the reaction time is 20-25 hours, the whole reaction is carried out in the air, the reaction condition is very mild, the reaction is easy to achieve, the safety is realized, and the health of experimenters is ensured. The yield of the method can reach 94% at most, a series of aryl acridine derivatives can be prepared, and the method has strong substrate universality and is popularized.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to an aryl acridine derivative synthesized by palladium catalysis and a preparation method thereof.
Background
The aryl acridine and the derivatives thereof are important organic compounds and have great application value and wide application prospect in the fields of biomedicine, food, cosmetics and organic electronic materials thereof.
In the prior art, the aryl acridine and the derivatives thereof are mainly prepared by the following methods: 1. preparing an aryl acridine derivative (Eur.J.org.chem.2017,577-581) by palladium-catalyzed cyclization of 2-aminobenzophenone and cyclohexanone; 2. 9-chloroacridine and arylboronic acid are used as raw materials, and a substitution reaction is carried out at 100 ℃ by using toluene as a solvent to prepare the arylacridine compound (chem. However, the above methods have some disadvantages in that the reaction conditions of the method 1 are very severe, and it is required to be performed under an oxygen atmosphere at 160 ℃, and the solvent used is TCE, which is a toxic solvent, and alcohol-like drunkenness may occur by low-dose inhalation. In the method 2, toxic POCl is needed to be used for synthesizing 9-chloroacridine3Or SOCl2Both the two have pungent odor and certain toxicity, which easily affect the health of experimenters, and the reaction has larger danger and is not in line with the green chemical development; due to the defects, the practicability and the applicability of the methods are greatly limited, and the methods cannot be really popularized on a large scale.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide the aryl acridine derivative synthesized by palladium catalysis and the preparation method thereof. In order to achieve the purpose, the invention provides the following technical scheme:
an aryl acridine derivative synthesized by palladium catalysis, the structural formula of which is
wherein-R1Is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
-R2is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
ar is any one of phenyl, m-chlorophenyl, p-bromophenyl, p-tert-butylphenyl and p-methoxyphenyl.
As a further improvement of the invention, the aryl acridine derivative is prepared by reacting a 2- (arylamino) benzonitrile derivative with aryl boric acid;
wherein the structural formula of the 2- (arylamino) benzonitrile derivative is shown in the specification
The structural formula of the arylboronic acid is
ArB(OH)2；
Which is of the formula
wherein-R in the 2- (arylamino) benzonitrile derivatives and arylacridine derivatives1The same, all are any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
-R in 2- (arylamino) benzonitrile derivatives and arylacridine derivatives2The same, all are any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
the arylboronic acid is any of phenyl, m-chlorophenyl, p-bromophenyl, p-tert-butylphenyl and p-methoxyphenyl, as in Ar in the arylacridine derivative.
As a further improvement of the invention, the reaction of the 2- (arylamino) benzonitrile derivative and the arylboronic acid is carried out in a solvent, and the solvent is water.
As a further improvement of the invention, when the 2- (arylamino) benzonitrile derivative and the arylboronic acid are reacted in a solvent, a palladium catalyst, an additive and a ligand are also added to the solvent.
As a further improvement of the invention, the palladium catalyst is any one of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate.
As a further development of the invention, the additive is methanesulfonic acid.
As a further improvement of the invention, the ligand is 2, 2' -bipyridine.
As a further improvement of the invention, the preparation method of the aryl acridine derivative synthesized by palladium catalysis is characterized in that: adding the 2- (arylamino) benzonitrile derivative, the arylboronic acid, the palladium catalyst, the ligand, the additive and the solvent into a reaction vessel in an air atmosphere, stirring and mixing, uniformly mixing, and reacting at the temperature of 90-110 ℃ for 20-25h to obtain the arylacridine derivative.
As a further improvement of the invention, the mass ratio of the 2- (arylamino) benzonitrile derivative to the arylboronic acid added to the reaction vessel is from 1:1.5 to 2.5.
As a further improvement of the present invention, the ratio of the amounts of the substances among the 2- (arylamino) benzonitrile derivative, the palladium catalyst, the ligand and the additive to be fed to the reaction vessel is 1: 0.05: 0.06: 2.
the invention has the beneficial effects that: the raw materials are easy to prepare, the sources are wide, and the cost is relatively low; the target product can be directly synthesized without separating intermediate products; the reaction condition is mild, the yield can reach 94 percent at most, the process engineering is greatly simplified, the energy consumption is reduced, and the method has the advantage of high yield; in addition, the waste solution is less in the reaction process, and other polluted gases and liquid are not discharged, so that the method reduces the discharge of the waste solution, and has the advantages of protecting the environment and ensuring the health of operators; the toxicity of the substances used in the invention is low, thus ensuring the health of operators; in addition, a series of aryl acridine derivatives can be prepared, the method has stronger substrate universality, and better guarantee is provided for developing organic compounds related to the aryl acridine derivatives
Drawings
FIG. 1 is a reaction scheme of example 1 of the present invention;
Detailed Description
Example 1
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), phenylboronic acid (0.75mmol), palladium acetate (5 mol%) as a palladium catalyst, 2, 2' -bipyridine (6 mol%), methanesulfonic acid (1.0mmol) and solvent water (2mL) into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 24 hours at the temperature of 100 ℃ to prepare 9-phenylacridine; the product yield was 94%;
characterization data:1H NMR(400MHz,CDCl3)δ8.34(d,J＝8.8Hz,2H),7.82(t,J＝7.9Hz,2H),7.77-7.75(m,2H),7.76-7.63(m,3H),7.50-7.45(m,4H)；13C NMR(100MHz,CDCl3) The structural formula of delta 148.8,147.2,136.0,130.4,130.0,129.6,128.5,128.4,126.9,125.6,125.2.9-phenylacridine is shown in the specification
Which is of the formula
Example 2
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), 3-chlorobenzeneboronic acid (0.75mmol), palladium acetate (5 mol%) serving as a palladium catalyst, 2' -bipyridine (6 mol%) serving as a ligand, methanesulfonic acid (1.0mmol) serving as an additive and solvent water (2mL) into a reaction vessel under an air atmosphere, and stirring and mixing; after being mixed evenly, the mixture reacts for 24 hours at the temperature of 100 ℃ to prepare 9- (3-chlorphenyl) acridine; the yield of the final product was 96%.
Characterization data:
1H NMR(400MHz,CDCl3)δ8.30(d,J＝8.8Hz,2H),7.81-7.77(m,2H),7.67(d,J＝8.7Hz，1H),7.48-7.44(m,3H),7.36-7.32(m,1H)；13C NMR(125MHz,CDCl3)δ148.8,145.6,130.8,134.0,134.8,130.6,130.3,130.0,129.8,128.8,127.8,126.6,126.2,125.1.
the structural formula of the 9- (3-chlorophenyl) acridine is as follows:
the reaction formula is as follows:
example 3
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), 4-methoxyphenylboronic acid (0.75mmol), palladium acetate (5 mol%) serving as a palladium catalyst, 2' -bipyridine (6 mol%) serving as a ligand, methanesulfonic acid (1.0mmol) serving as an additive and water (2mL) serving as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 24 hours at the temperature of 100 ℃ to prepare 9- (4-methoxyphenyl) acridine; the yield of the final product was 90%.
Characterization data:1H NMR(500MHz,CDCl3)δ8.27(d,J＝8.9Hz,2H),7.77-7.76(m,4H),7.13(d,J＝8.3Hz,2H),3.94(S,3H)；13C NMR(125MHz,CDCl3)δ159.9,149.1,147.3,131.9,130.0,129.8,128.2,127.1,125.7,125.6,114.1,55.6.
the structural formula of the 9- (4-methoxyphenyl) acridine is as follows:
the reaction formula is as follows:
example 4
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), 4-isopropylphenylboronic acid (0.75mmol) and palladium acetate (5 mol%) serving as a palladium catalyst, 2' -bipyridyl (6 mol%) serving as a ligand, methanesulfonic acid (1.0mmol) serving as an additive and water (2mL) serving as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 24 hours at the temperature of 100 ℃ to prepare 9- (4-isopropylphenyl) acridine; the yield of the final product was 91%.
Characterization data:1H NMR(500MHz,CDCl3)δ8.28(d,J＝8.28Hz,2H),7.79-7.75(m,4H),7.47-7.40(m,4H),7.37-7.35(m,2H),3.12-3.05(m,1H),1.40(d,J＝6.9Hz,6H)；13C NMR(125MHz,CDCl3)δ149.2,148.9,147.8,133.3,130.6,130.1,129.7,127.2,126.6,125.6,125.5,34.2,24.2.
the structural formula of the 9- (4-isopropylphenyl) acridine is as follows:
the reaction formula is as follows:
example 5
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), 4-bromobenzeneboronic acid (0.75mmol) and palladium catalyst palladium acetate (5 mol%), ligand 2, 2' -bipyridine (6 mol%), additive methanesulfonic acid (1.0mmol) and solvent water (2mL) into a reaction vessel under an air atmosphere, and stirring and mixing; after being mixed evenly, the mixture reacts for 22 hours at the temperature of 110 ℃ to prepare 9- (4-bromophenyl) acridine; the yield of the final product was 90%. Characterization data:1H NMR(500MHz,CDCl3)δ8.29(d,J＝8.8Hz,2H),7.80-7.74(m,4H),7.67(d,J＝8.7Hz,2H),7.44(t,J＝7.4Hz,2H),7.32(d,J＝8.2Hz,2H)；13C NMR(125MHz,CDCl3)δ148.8,145.9,135.0,132.3,131.9,130,3,129.8,126.6,126.1,125.1,123.0.
the structural formula of the 9- (4-bromophenyl) acridine is as follows:
the reaction formula is as follows:
example 6
Adding raw materials of 2- (phenylamino) benzonitrile (0.5mmol), 4-tert-butylbenzoic acid (0.75mmol) and palladium catalyst palladium acetate (5 mol%), ligand 2, 2' -bipyridine (6 mol%), additive methanesulfonic acid (1.0mmol) and solvent water (2mL) into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 25 hours at the temperature of 110 ℃ to prepare 9- (4-tert-butylphenyl) acridine; the yield of the final product was 86%.
Characterization data:1H NMR(400MHz,CDCl3)δ8.32-8.28(m,2H),7.80-7.75(m,4H),7.63-7.60(m,2H),7.45-7.36(m,4H),1.46(s,9H)；13C NMR(125MHz,CDCl3)δ151.5,148.9,147.8,133.0,130.4,130.1,129.7,127.2,125.6,125.5,125.4,35.0,31.6.
the structural formula of 9- (4-tert-butylphenyl) acridine is as follows:
the reaction formula is as follows:
example 7
Adding 2- (m-methylanilino) benzonitrile (0.5mmol), phenylboronic acid (0.75mmol), palladium acetate (5 mol%) as a palladium catalyst, 2' -bipyridine (6 mol%) as a ligand, methanesulfonic acid (1.0mmol) as an additive and water (2mL) as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 20 hours at the temperature of 90 ℃ to prepare 3-methyl-9-phenylacridine; the yield of the final product was 88%. Characterization data:1H NMR(400MHz,CDCl3)δ8.20-8.18(m,2H),7.74-7.69(m,1H),7.65-7.63(m,1H),7.58-7.52(m,4H),7.49-7.48(m,1H),7.40-7.38(m,2H),7.35-7.31(m,1H),7.08-7.05(m,1H),3.99(s,3H)；13C NMR(125MHz,CDCl3)δ161.4,150.6,149.0,147.1,136.1,130.4,130.0,128.9,128.5,128.4,128.1,126.9,124.6,124.2,121.3,121.0,105.3,55.6.
the structural formula of the 3-methyl-9-phenylacridine is as follows:
which is of the formula
Example 8
Adding 2- (m-methoxyphenylamino) benzonitrile (0.5mmol), phenylboronic acid (0.75mmol), palladium acetate (5 mol%) as a palladium catalyst, 2' -bipyridine (6 mol%) as a ligand, methanesulfonic acid (1.0mmol) as an additive and water (2mL) as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 24 hours at the temperature of 100 ℃ to prepare 3-methoxy-9-phenylacridine; the yield of the final product was 85%. Characterization data: 1H NMR (cdcl3,400mhz, ppm): δ 8.19(d, J ═ 8.5Hz,1H),7.74-7.73(m,1H),7.65-7.63(m,1H),7.58-7.52(m,4H),7.49(d, J ═ 2.9Hz,1H),7.40-7.38(m,2H),7.35-7.31(m,1H),7.07(dd, J ═ 2.5Hz, J ═ 9.5Hz,1H),3.99(s, 3H); 13C NMR (CDCl3,125MHz, ppm): delta 161.2,150.7,149.0,147.1,136.1,130.4,130.0,129.0,128.5,128.4,128.1,127.0,124.7,124.3,121.4,121.0,105.3,55.7.
The structural formula of the 3-methoxy-9-phenylacridine is as follows:
which is of the formula
Example 9
Adding 2- (o-methylanilino) benzonitrile (0.5mmol), phenylboronic acid (0.75mmol), palladium acetate (5 mol%) as a palladium catalyst, 2' -bipyridine (6 mol%) as a ligand, methanesulfonic acid (1.0mmol) as an additive and water (2mL) as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being uniformly mixed, the mixture reacts for 23 hours at the temperature of 90 ℃ to prepare 2-methyl-9-phenylacridine; the yield of the final product was 92%. Characterization data: 1H NMR (cdcl3,400mhz, ppm): δ 8.33(d, J ═ 8.8Hz,1H),7.77-7.73(m,1H),7.69-7.66(m,1H),7.62-7.54(m,5H),7.45-7.40(m,3H),7.33-7.29(m,1H),3.01(s, 3H); 13C NMR (CDCl3,125MHz, ppm) delta 148.5,148.2,147.0,137.5,136.7,130.6,130.4,129.5,129.3,128.5,128.3,126.8,125.6,125.5,125.2,125.1,125.0, 18.8;
the structural formula of the 2-methyl-9-phenylacridine is as follows:
which is of the formula
Example 10
Adding 2- (m-tert-butylanilino) benzonitrile (0.5mmol), phenylboronic acid (0.75mmol), palladium acetate (5 mol%) as a palladium catalyst, 2' -bipyridine (6 mol%) as a ligand, methanesulfonic acid (1.0mmol) as an additive and water (2mL) as a solvent into a reaction vessel under an air atmosphere, and stirring and mixing; after being mixed evenly, the mixture reacts for 22 hours at the temperature of 100 ℃ to prepare 3-methoxy-9-phenylacridine; the yield of the final product was 85%. Characterization data: 1H NMR (cdcl3,400mhz, ppm): δ 8.27(d, J ═ 8.7Hz,1H),8.22-8.21(m,1H),7.77-7.73(m,1H),7.70(d, J ═ 8.7Hz,1H),7.65(d, J ═ 9.2Hz,1H),7.60-7.56(m,3H),7.54-7.51(m,1H),7.44-7.37(m,3H),1.46(s, 9H); 13CNMR (CDCl3,125MHz, ppm): delta 153.3,149.3,149.0,146.8,136.2,130.6,129.9,129.5,128.5,128.4,126.9,126.5,125.3,125.1,124.2,123.6,35.4,31.0
The structural formula of the 3-tert-butyl-9-phenylacridine is as follows:
which is of the formula
FIG. 1 is a reaction scheme of example 1 of the present invention:
mechanism description, taking example 1 as an example: the reaction of the substrate 2- (phenylamino) benzonitrile 1a with phenylboronic acid to give 9-phenylacridine is an example, and a possible mechanism of the reaction is proposed. Firstly, phenylboronic acid reacts with a palladium catalyst to generate an active phenyl palladium species A, the active phenyl palladium species A is coordinated with a substrate 2- (phenylamino) benzonitrile to form an intermediate B, and then a phenyl-palladium bond is further inserted into C [ identical to ] N to form an intermediate C. Hydrolysis under acidic conditions forms intermediate D and palladium species. The intermediate D can further generate intramolecular Friedel-crafts acylation reaction to generate an intermediate E. And finally, further dehydrating the E to form the target product 9-phenylacridine.
The aryl acridine derivative synthesized by palladium catalysis and the preparation method thereof are prepared by taking a 2- (arylamino) benzonitrile derivative and aryl boric acid as reactants for reaction; wherein the structural formula of the 2- (arylamino) benzonitrile derivative is shown in the specification
wherein-R1Is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl; -R2Is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl; and the aryl boric acid has the structural formula of ArB (OH)2(ii) a Ar is any one of phenyl, m-chlorophenyl, p-bromophenyl, p-tert-butylphenyl and p-methoxyphenyl; the reactant has wide sources, easy preparation, low cost, low toxicity and little influence on human health. The reaction of the invention is carried out in a solvent, and the solvent is water; compared with substances such as benzene, toluene, N, N-dimethylacetamide and the like as solvents, the water is used as the solvent, so that the source is wide and the cost is low; on the other hand, the method is nontoxic and harmless, green and environment-friendly, meets the requirement of green chemical development, and in addition, palladium is also added into a solvent during reactionCatalysts, additives and ligands; the palladium catalyst is any one of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate, preferably palladium acetate, and under the action of the catalyst, the reaction rate can be greatly accelerated, and the reaction time can be shortened; the ratio of the amount of the palladium catalyst to the amount of the 2- (arylamino) benzonitrile derivative added in the present invention is 0.05: 1; the additive is methanesulfonic acid, and the function of the additive is to enable the whole reaction environment to be in an acid environment, so that the reaction is favorably carried out; the ligand is 2, 2' -bipyridyl, and the yield of the invention can be further improved under the action of the ligand. The reaction temperature of the invention is 90-110 ℃, the reaction time is 20-25 hours, the whole reaction is carried out in the air, the reaction condition is very mild, the reaction is easy to reach, and the invention is safe, thereby ensuring the health of experimenters.
The method can directly synthesize the target product in one step, does not need to separate intermediate products, can obtain the target product only by stirring and reacting under normal pressure, has the highest yield of 94 percent, greatly simplifies process engineering, reduces energy consumption and has the advantage of high yield; in addition, the waste solution is less in the reaction process, and other polluted gases and liquid are not discharged, so that the method reduces the discharge of the waste solution, and has the advantages of protecting the environment and ensuring the health of operators; the toxicity of the substances used in the invention is low, thus ensuring the health of operators; in addition, a series of aryl acridine derivatives can be prepared, and the method has stronger substrate universality and provides better guarantee for developing organic compounds related to the aryl acridine derivatives.
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (10)
1. An aryl acridine derivative synthesized by palladium catalysis, which is characterized in that: the structural formula of the aryl acridine derivative is shown in the specification
wherein-R1Is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
-R2is any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
ar is any one of phenyl, m-chlorophenyl, p-bromophenyl, p-tert-butylphenyl and p-methoxyphenyl.
2. The palladium-catalyzed synthetic arylacridine derivative according to claim 1, wherein: the aryl acridine derivative is prepared from
2- (arylamino) benzonitrile derivatives and
aryl boric acid;
wherein the structural formula of the 2- (arylamino) benzonitrile derivative is shown in the specification
The structural formula of the arylboronic acid is
ArB(OH)2；
Which is of the formula
wherein-R in the 2- (arylamino) benzonitrile derivatives and arylacridine derivatives1The same, all are any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
-R in 2- (arylamino) benzonitrile derivatives and arylacridine derivatives2The same, all are any one of hydrogen, methyl, methoxy, halogen and trifluoromethyl;
the arylboronic acid is any of phenyl, m-chlorophenyl, p-bromophenyl, p-tert-butylphenyl and p-methoxyphenyl, as in Ar in the arylacridine derivative.
3. The palladium-catalyzed synthetic arylacridine derivative according to claim 2, wherein: the reaction of the 2- (arylamino) benzonitrile derivative and the arylboronic acid is carried out in a solvent, and the solvent is water.
4. The palladium-catalyzed synthetic arylacridine derivative according to claim 3, wherein: when the 2- (arylamino) benzonitrile derivative and the arylboronic acid react in the solvent, a palladium catalyst, an additive and a ligand are also added into the solvent.
5. The palladium-catalyzed synthetic arylacridine derivative according to claim 4, wherein: the palladium catalyst is any one of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate.
6. The palladium-catalyzed synthetic arylacridine derivative according to claim 5, wherein: the additive is methanesulfonic acid.
7. The palladium-catalyzed synthetic arylacridine derivative according to claim 6, wherein: the ligand is 2, 2' -bipyridine.
8. The method for preparing an arylacridine derivative synthesized by palladium catalysis according to claim 7, wherein: adding a 2- (arylamino) benzonitrile derivative, arylboronic acid, a palladium catalyst, a ligand, an additive and a solvent into a reaction vessel in an air atmosphere, and stirring and mixing; after being mixed evenly, the mixture reacts for 20 to 25 hours at the temperature of between 90 and 110 ℃ to prepare the aryl acridine derivative.
9. The method for preparing an arylacridine derivative synthesized by palladium catalysis according to claim 8, wherein: the mass ratio of the 2- (arylamino) benzonitrile derivative to the arylboronic acid added to the reaction vessel is from 1:1.5 to 2.5.
10. The method for preparing an arylacridine derivative synthesized by palladium catalysis according to claim 9, wherein: the ratio of the amounts of the 2- (arylamino) benzonitrile derivative, the palladium catalyst, the ligand and the additive to the amount of the substance added to the reaction vessel was 1: 0.05: 0.06: 2.
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| CN102675203A (en) * | 2012-05-09 | 2012-09-19 | 常州大学 | Preparation method of acridine compounds |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111960987A (en) * | 2020-08-11 | 2020-11-20 | 温州大学 | Synthesis method of methylene bis (isoindole) compound |
| CN111960987B (en) * | 2020-08-11 | 2022-02-11 | 温州大学 | Synthesis method of methylene bis (isoindole) compound |
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