CN108774169B - 8-hydroxyquinoline compound and preparation method thereof - Google Patents
8-hydroxyquinoline compound and preparation method thereof Download PDFInfo
- Publication number
- CN108774169B CN108774169B CN201810800844.2A CN201810800844A CN108774169B CN 108774169 B CN108774169 B CN 108774169B CN 201810800844 A CN201810800844 A CN 201810800844A CN 108774169 B CN108774169 B CN 108774169B
- Authority
- CN
- China
- Prior art keywords
- hydroxyquinoline
- reaction
- hydroxyquinoline compound
- aldehyde
- aminophenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an 8-hydroxyquinoline compound and a preparation method thereof, wherein the structural formula of the 8-hydroxyquinoline compound is as follows:
(ii) a Wherein R is1And R2Each independently selected from an alkane, cycloalkane, phenyl, substituted phenyl or heterocycloarene; the substituent in the substituted phenyl is independently selected from any one or combination of more than two of alkyl, alkoxy, hydroxyl, halogen and ester group; the preparation method comprises the following steps: in the air atmosphere, a uniformly mixed reaction system of 2-aminophenol, aldehyde, alkyne, catalyst and organic solvent is reacted for 0.5 to 4 hours at the temperature of 60 to 110 ℃, and the reaction solution after the reaction is subjected to post-treatment to obtain the target product 8-hydroxyquinoline compoundThe environmental cost is greatly reduced; simple operation, high yield and wide substrate universality, and perfects and enriches the construction of 8-hydroxyquinoline compound molecular libraries.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an 8-hydroxyquinoline compound and a preparation method thereof.
Background
The 8-hydroxyquinoline compound is an important organic synthesis intermediate and has wide application in the chemical, pharmaceutical and medical fields. The 8-hydroxyquinoline compound is used as a metal ion chelating agent with excellent performance, and is widely applied to metal element chemical analysis, metal ion extraction, photometric analysis and metal corrosion prevention in metallurgical industry and analytical chemistry; as most of the 8-hydroxyquinoline and the derivatives have biological activity, the derivatives are raw materials for synthesizing important medicaments such as kexiening, halogenated quinoline anti-ameba medicaments and the like, and have wide application in the field of medical industry; 8-hydroxyquinoline is directly used as a disinfectant, and halogenated derivatives, nitration and N-oxide thereof are raw materials for synthesizing medicaments and are also used as intermediates for synthesizing pesticides, dyes and other functional materials; 8-hydroxyquinoline is bonded on the polymer resin to ensure that the polymer resin is high in molecular weight, and has wide application prospects in the aspects of analysis, environment, materials, electroluminescence, conductive polymers and the like.
Therefore, many people have attracted attention to research and development of synthetic methods of such compounds, and four methods of quinoline sulfonation base fusion, chloroquinoline hydrolysis, aminoquinoline hydrolysis and Skraup synthesis have been reported in the literature.
However, these methods have the following problems, method (1): a large amount of acid and alkali are needed in the process of the sulfonation and alkali fusion, the amount of wastewater is large, and the environment is seriously polluted; method (2): the required raw material 8-chloroquinoline is prepared from o-chloroaniline, but the o-chloroaniline has high toxicity and high corrosivity in alkaline hydrolysis of chlorine-containing organic matters; method (3): the required raw material 8-aminoquinoline is reduced by 8-nitroquinoline, but two isomers of 5-nitroquinoline and 8-nitroquinoline are obtained in the mixed acid nitration process of quinoline and are not easy to separate; method (4): the 8-hydroxyquinoline is obtained by co-heating o-aminophenol, concentrated sulfuric acid, glycerol and o-nitrophenol, the method needs to be carried out at high temperature, and the environment is polluted by tar generated by pyrolysis of the glycerol.
It is necessary to develop a method for synthesizing 8-hydroxyquinoline compounds, which is efficient, wide in raw material source, simple and convenient to operate and environment-friendly.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an 8-hydroxyquinoline compound and a preparation method thereof, and the method for synthesizing the 8-hydroxyquinoline compound in series by a multi-component one-pot method has the advantages of simple and convenient raw material source, simple operation, continuous reaction, atom economy and environmental friendliness.
In order to solve the technical problems, the invention adopts the following technical scheme:
an 8-hydroxyquinoline compound, which has the following structural formula:
wherein R is1And R2Each independently selected from an alkane, cycloalkane, phenyl, substituted phenyl or heterocycloarene; the substituent in the substituted phenyl is independently selected from any one or combination of more than two of alkyl, alkoxy, hydroxyl, halogen and ester group; the number of the substituent groups is 1 or more than 1; the position of the substituent is ortho-position, meta-position or para-position.
The preparation method of the 8-hydroxyquinoline compound comprises the following steps: in the air atmosphere, reacting a uniformly mixed reaction system of 2-aminophenol, aldehyde, alkyne, catalyst and organic solvent at 60-110 ℃ for 0.5-4h, and carrying out post-treatment on the reaction solution after the reaction to obtain the target product 8-hydroxyquinoline compound.
The structure of the 2-aminophenol is shown as a formula (I), the structure of the aldehyde is shown as a formula (II), the structure of the alkyne is shown as a formula (III),
wherein, in the formula (II) or the formula (III), R1And R2Each independently selected from an alkane, cycloalkane, phenyl, substituted phenyl or heterocycloarene; the substituent in the substituted phenyl is independently selected from any one or combination of more than two of alkyl, alkoxy, hydroxyl, halogen and ester group; the number of the substituent groups is 1 or more than 1; the position of the substituent is ortho-position, meta-position or para-position.
The molar ratio of the 2-aminophenol to the aldehyde to the alkyne is (1.1-1.5) to 1 (1.2-2).
The catalyst comprises a transition metal catalyst and a Bronsted acid catalyst; the transition metal catalyst comprises one of silver trifluoromethanesulfonate, copper trifluoromethanesulfonate and gold chloride; the Bronsted acid catalyst comprises one of glacial acetic acid, trifluoroacetic acid and trifluoromethanesulfonic acid.
The molar ratio of the transition metal catalyst to the aldehyde is 0.5-5: 100, respectively; the molar ratio of the Bronsted acid catalyst to the aldehyde is 2-4: 1.
The organic solvent is one of toluene, 1, 2-dichloroethane, acetonitrile, methanol and 1, 4-dioxane.
The post-treatment method of the reaction liquid comprises the following steps: and after the reaction is finished, evaporating the solvent under reduced pressure, washing with an alkaline solution, extracting with ethyl acetate or dichloromethane, separating and purifying by adopting column chromatography, and performing gradient elution by using petroleum ether/ethyl acetate as an eluent to obtain the 8-hydroxyquinoline compound.
The invention has the beneficial effects that: the invention adopts a multi-component one-pot method, the raw material source is simple, convenient and quick, the catalyst dosage is low, and the environmental cost is greatly reduced; simple operation, high yield and wide substrate universality, and perfects and enriches the construction of 8-hydroxyquinoline compound molecular libraries. The beneficial effect of the invention is realized by the concerted catalysis of transition metal and Bronsted acid. Specifically, under the action of Bronsted acid, 2-aminophenol and aromatic aldehyde or aliphatic aldehyde generate imine intermediate. Simultaneously, the transition metal activates the terminal alkyne to generate a metal-alkyne active intermediate with nucleophilic property. Further, under the action of the Bronsted acid, the nucleophilic addition-cyclization-oxidation tandem process of the metal-alkyne active intermediate to the activated imine finally generates the 8-hydroxyquinoline compound. The addition of the Bronsted acid is beneficial to the generation of an imine intermediate, and the introduction of the transition metal is convenient for the generation of a metal-alkyne active intermediate. The synergistic catalytic action of the two components is beneficial to the rapid construction of the 8-hydroxyquinoline skeleton.
Drawings
FIG. 1 is a single crystal diffractogram of 4g of 8-hydroxyquinoline;
FIG. 2 is a single crystal diffractogram of 8-hydroxyquinoline compound 4 i;
FIG. 3 is a nuclear magnetic resonance H spectrogram of 8-hydroxyquinoline compound 4 v;
FIG. 4 is a nuclear magnetic resonance C spectrum of 8-hydroxyquinoline compound 4 v;
FIG. 5 is a nuclear magnetic resonance H spectrogram of 8-hydroxyquinoline compound 4 x;
FIG. 6 is the nuclear magnetic resonance C spectrum of 8-hydroxyquinoline compound 4 x.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given numerous insubstantial modifications and adaptations by those skilled in the art based on the teachings set forth above.
Example 1
The synthesis method of 8-hydroxyquinoline compound 4a in this example is as follows:
to a dichloroethane (4mL) solution containing AgOTf (0.5 mol%) were added o-aminophenol (1.1mmol), benzaldehyde (1mmol) and phenylacetylene (1.2mmol) in this order, and after stirring well at room temperature, trifluoroacetic acid (4mmol) was added and the temperature was raised to 80 ℃ for reaction. The reaction was monitored by TLC to completion, and after addition of 20mL of dichloromethane, washed with water, dried over anhydrous sodium sulfate and column chromatographed (PE/EA ═ 20:1 as eluent) to give 280mg of pale yellow solid powder in 94% yield.
1H NMR(600MHz,CDCl3)8.16-8.20(m,2H),7.85(s,1H),7.46-7.58(m,8H),7.37-7.40(m,2H),7.21(d,J＝8.7Hz,1H)ppm；13C NMR(150MHz,CDCl3)152.0,150.2,147.3,136.4,136.2,135.8,127.2,127.1,126.9,126.5,126.1,125.8,125.0,124.8,123.2,123.6,123.5,117.5,113.6,107.6ppm.
Example 2
The synthesis method of 8-hydroxyquinoline compound 4b in this example is as follows:
to a solution of AgOTf (0.5 mol%) in toluene (4mL) were added o-aminophenol (1.2mmol), p-tolualdehyde (1mmol) and phenylacetylene (1.3mmol) in this order, and after stirring well at room temperature, trifluoroacetic acid (3mmol) was added and the temperature was raised to 80 ℃ for reaction. The reaction was run to completion by TLC plate, and after removal of toluene by concentration, 20mL of dichloromethane was added, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (PE/EA ═ 20:1 as eluent) to give 286mg of pale yellow solid in 92% yield.
1H NMR(600MHz,CDCl3)8.09(d,J＝8.2Hz,2H),7.84(s,1H),7.55(ddd,J＝22.1,11.4,4.4Hz,5H),7.33-7.39(m,4H),7.20(dd,J＝6.1,2.6Hz,1H),2.45(s,3H)ppm；13C NMR(150MHz,CDCl3)153.4,151.4,148.5,138.8,137.5,137.3,134.9,128.7,128.6,128.4,128.3,127.6,127.5,126.4,126.2,126.1,124.8,118.7,114.9,108.8,20.3ppm.
Example 3
The synthesis method of 8-hydroxyquinoline compound 4c in this example is as follows:
to a dioxane (4mL) solution containing AgOTf (1 mol%) were added sequentially o-aminophenol (1.1mmol), 2,4, 6-trimethylbenzaldehyde (1mmol) and phenylacetylene (1.5mmol), and after stirring at room temperature, trifluoroacetic acid (1mmol) was added, and the mixture was heated to 110 ℃ for reaction. The reaction was run to completion by TLC plate, concentrated to remove dioxane, added 20mL dichloromethane, washed with water, dried over anhydrous sodium sulfate, and column chromatographed (PE/EA 15:1 as eluent) to give 298mg of a pale yellow solid in 88% yield.
1H NMR(600MHz,CDCl3)7.55-7.58(m,2H),7.53(t,J＝7.3Hz,2H),7.47-7.51(m,2H),7.41-7.45(m,1H),7.35(s,1H),7.19-7.22(m,1H),7.01(s,2H),2.37(s,3H),2.11(s,6H)ppm；13C NMR(150MHz,CDCl3)156.6,151.5,147.9,137.0,136.9,134.8,128.5,127.5,127.5,127.4 126.4,124.4,108.7,20.1,19.3ppm.
Example 4
The synthesis method of 8-hydroxyquinoline compound 4d in this example is as follows:
to a solution of dichloroethane (4mL) containing AgOTf (0.5 mol%) were added o-aminophenol (1.1mmol), p-bromobenzaldehyde (1mmol) and phenylacetylene (1.2mmol) in this order, and after stirring well at room temperature, trifluoroacetic acid (2mmol) was added and the temperature was raised to 70 ℃ for reaction. The reaction was run to completion by TLC plate, and after addition of 20mL dichloromethane, washed with water, dried over anhydrous sodium sulfate and column chromatographed (PE/EA ═ 20:1 as eluent) to give 360mg of pale yellow solid in 96% yield.
1H NMR(600MHz,CDCl3)8.06(d,J＝8.3Hz,2H),7.81(s,1H),7.66(d,J＝8.2Hz,2H),7.55(d,J＝5.4Hz,5H),7.40(d,J＝6.0Hz,2H),7.21(d,J＝2.4Hz,1H)ppm；13CNMR(150MHz,CDCl3)153.2,152.5,150.0,138.6,138.1,137.6,132.3,132.1,129.5,129.3,129.0,128.9,127.8,127.7,126.1,124.2,119.5,116.1,110.2ppm.
Example 5
The synthesis method of 8-hydroxyquinoline compound 4e in this example is as follows:
to a solution of dichloroethane (4mL) containing AgOTf (0.5 mol%) were added o-aminophenol (1.1mmol), p-bromobenzaldehyde (1mmol) and phenylacetylene (1.2mmol) in this order, and after stirring well at room temperature, trifluoroacetic acid (2mmol) was added and the temperature was raised to 70 ℃ for reaction. The reaction was run to completion by TLC plate, 20mL of dichloromethane was added, washed with water, dried over anhydrous sodium sulfate, and column chromatographed (PE/EA ═ 20:1 as eluent) to give 355mg of pale yellow solid in 95% yield.
1H NMR(600MHz,CDCl3)8.47(s,1H),8.34(t,J＝1.6Hz,1H),8.10(d,J＝7.8Hz,1H),7.81(s,1H),7.61(d,J＝8.0Hz,1H),7.55-7.57(m,3H),7.50-7.540(m,1H),7.40(dd,J＝8.8,6.2Hz,3H),7.23(dd,J＝6.0,2.7Hz,1H)ppm；13C NMR(100MHz,CDCl3)152.8,152.6,150.1,140.8,138.6,138.1,132.5,130.4,129.5,128.7,127.8,126.2,125.9,123.2,119.7,116.1,110.3ppm.
Example 6
The synthesis method of 8-hydroxyquinoline compound 4f in this example is as follows:
to a solution of dichloroethane (4mL) containing AgOTf (0.5 mol%) were added o-aminophenol (1.1mmol), p-bromobenzaldehyde (1mmol) and phenylacetylene (1.2mmol) in this order, and after stirring well at room temperature, trifluoroacetic acid (2mmol) was added and the temperature was raised to 70 ℃ for reaction. The reaction was run to completion by TLC plate, 20mL of dichloromethane was added, washed with water, dried over anhydrous sodium sulfate, and column chromatographed (PE/EA ═ 20:1 as eluent) to give 350mg of pale yellow solid in 95% yield.
1H NMR(600MHz,CDCl3)7.72-7.75(m,2H),7.69(dd,J＝7.6,1.6Hz,1H),7.57-7.61(m,2H),7.49-7.55(m,3H),7.42-7.49(m,3H),7.32(td,J＝7.8,1.7Hz,1H),7.22(dd,J＝7.1,1.5Hz,1H)ppm.
Example 7
The synthesis of 4g of 8-hydroxyquinoline compound in this example is as follows:
to a dioxane (4mL) solution containing AgOTf (1 mol%), o-aminophenol (1.2mmol), p-bromobenzaldehyde (1mmol) and phenylacetylene (1.5mmol) were added in this order, and after stirring well at room temperature, trifluoroacetic acid (4mmol) was added and the temperature was raised to 100 ℃ for reaction. The reaction was run to completion by TLC plate, concentrated to remove dioxane, and then 20mL dichloromethane was added, washed with water, dried over anhydrous sodium sulfate, and column chromatographed (PE/EA 15:1 as eluent) to give 307mg of pale yellow solid in 86% yield.
1H NMR(600MHz,CDCl3)8.25(d,J＝8.3Hz,2H),8.19(d,J＝8.4Hz,2H),7.88(s,1H),7.55(m,5H),7.41(d,J＝6.5Hz,2H),7.23(dd,J＝6.1,2.5Hz,1H),3.97(s,3H)ppm；13C NMR(100MHz,CDCl3)166.8,153.1,152.6,150.0,142.8,138.6,138.0,130.9,130.1,129.5(s),128.7,128.6,128.0,127.3,126.3,119.9,116.1,110.3,52.3ppm.
Example 8
The synthesis method of the 8-hydroxyquinoline compound 4h in the embodiment is as follows:
adding o-aminophenol (1.5mmol), isovaleraldehyde (1mmol) and phenylacetylene (2mmol) into dichloroethane (4mL) solution containing AgOTf (2 mol%), stirring at room temperature, adding trifluoroacetic acid (4mmol), and heating to 80 ℃ for reaction. The reaction was run to completion by TLC plate, after addition of 20mL dichloromethane, washed with water, dried over anhydrous sodium sulfate and column chromatographed (PE/EA ═ 30:1 as eluent) to give 252mg of a pale yellow solid in 86% yield.
1H NMR(600MHz,CDCl3)7.46-7.52(m,5H),7.32-37(m,2H),7.23(s,1H),7.15(d,J＝7.0Hz,1H),2.85(d,J＝7.2Hz,2H),2.27(dt,J＝13.5,6.7Hz,1H),1.00(d,J＝6.6Hz,6H)ppm；13C NMR(151MHz,CDCl3)158.8,151.4,148.2,137.6,137.5,128.9,127.8,127.7,125.9,124.7,122.4,47.1,29.2,28.5,21.9ppm.
By adopting the technical scheme of the invention, the synthesized 8-hydroxyquinoline compound is as follows:
the foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (3)
1. A preparation method of 8-hydroxyquinoline compounds is characterized by comprising the following steps: in the air atmosphere, reacting a uniformly mixed reaction system of 2-aminophenol, aldehyde, alkyne, catalyst and organic solvent for 0.5-4h at 60-110 ℃, and carrying out post-treatment on reaction liquid after the reaction is finished to obtain a target product, namely an 8-hydroxyquinoline compound, wherein the structural formula is as follows:
the structure of the 2-aminophenol is shown as a formula (I), the structure of the aldehyde is shown as a formula (II), the structure of the alkyne is shown as a formula (III),
wherein R is1And R2Each independently selected from an alkane, cycloalkane, phenyl, substituted phenyl or heterocycloarene; the substituent in the substituted phenyl is independently selected from any one or combination of more than two of alkyl, alkoxy, hydroxyl, halogen and ester group; the number of the substituent groups is 1 or more than 1; the position of the substituent is ortho-position, meta-position or para-position;
the molar ratio of the 2-aminophenol to the aldehyde to the alkyne is (1.1-1.5) to 1 (1.2-2);
the catalyst adopts silver trifluoromethanesulfonate and trifluoroacetic acid, and the molar ratio of the silver trifluoromethanesulfonate to aldehyde is (0.5-5): 100; the molar ratio of the trifluoroacetic acid to the aldehyde is (2-4) to 1.
2. The method for producing an 8-hydroxyquinoline compound according to claim 1, characterized in that: the organic solvent is one of toluene, 1, 2-dichloroethane, acetonitrile, methanol and 1, 4-dioxane.
3. The method for producing an 8-hydroxyquinoline compound according to claim 1, characterized in that: the post-treatment method of the reaction liquid comprises the following steps: and after the reaction is finished, evaporating the solvent under reduced pressure, washing with an alkaline solution, extracting with ethyl acetate or dichloromethane, separating and purifying by adopting column chromatography, and performing gradient elution by using petroleum ether/ethyl acetate as an eluent to obtain the 8-hydroxyquinoline compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810800844.2A CN108774169B (en) | 2018-07-20 | 2018-07-20 | 8-hydroxyquinoline compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810800844.2A CN108774169B (en) | 2018-07-20 | 2018-07-20 | 8-hydroxyquinoline compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108774169A CN108774169A (en) | 2018-11-09 |
| CN108774169B true CN108774169B (en) | 2020-12-25 |
Family
ID=64030121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810800844.2A Active CN108774169B (en) | 2018-07-20 | 2018-07-20 | 8-hydroxyquinoline compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108774169B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824588A (en) * | 2019-03-07 | 2019-05-31 | 浙江农林大学暨阳学院 | A kind of palladium chtalyst prepares 2,4- diphenyl -8-hydroxyquinoline class compound method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106316949A (en) * | 2016-08-19 | 2017-01-11 | 中国科学院上海有机化学研究所 | [18F] fluorine-labeled isoquinoline compounds and preparation method thereof |
-
2018
- 2018-07-20 CN CN201810800844.2A patent/CN108774169B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106316949A (en) * | 2016-08-19 | 2017-01-11 | 中国科学院上海有机化学研究所 | [18F] fluorine-labeled isoquinoline compounds and preparation method thereof |
Non-Patent Citations (7)
Also Published As
| Publication number | Publication date |
|---|---|
| CN108774169A (en) | 2018-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108033922B (en) | Preparation method of 3-acyl quinoxalinone derivative | |
| CN111690947B (en) | Electrochemical synthesis method of trifluoromethylated aryl amide derivative | |
| CN107501169A (en) | A kind of trans diarylethene LSD1 inhibitor, its preparation method and application | |
| CN108218672A (en) | Application of the metal compound/palladium compound catalytic reduction system in de- allyl reaction and deuterated reaction | |
| CN108774169B (en) | 8-hydroxyquinoline compound and preparation method thereof | |
| Liu et al. | Oxidative C–H functionalization of N-carbamoyl 1, 2-dihydroquinolines | |
| Dvorko et al. | Superbase‐Catalyzed Steric‐Hindrance‐Induced Dimerization of Alkynones to Highly Functionalized Furans | |
| CN102875421A (en) | Aziridine compound loop opening method based on p-nitrobenzoic acid | |
| CN112409275B (en) | Preparation method of photocatalytic 3-acylquinoxalinone compound | |
| CN115054599B (en) | Application of 2-aminoindole compounds in antitumor drugs | |
| Li et al. | AlCl3-Catalyzed Intramolecular Hydroarylation of Arenes with Alkynes | |
| CN112174962A (en) | Synthesis method of benzo [ e ] pyridylimidazo [4,5-g ] isoindole-1, 3(2H) -diketone compound | |
| Gao et al. | H2SO4-Mediated Intramolecular Cyclization of N-Arylated Homoallylamines: A Solvent-Free, Atom-and Step-Economical Synthesis of Tetrahydro-1-benzazepines | |
| CN108409648B (en) | Preparation method of sorafenib tosylate related intermediate | |
| CN108178758A (en) | 2- phenylimidazoles simultaneously [1,2-a] pyrido quinoxaline -2（1H）The synthetic method of -one derivative | |
| CN104860880A (en) | Method for synthesizing 8-(nitro methyl) quinoline compounds | |
| Hirner et al. | Convenient Access to Cycloalk-2-enone-Derived N-Sulfonyl Imines | |
| CN109535046A (en) | A kind of preparation method of sulfoxide compound | |
| Derieg et al. | 3-Amino-3, 4-dihydroquinazolines | |
| CN111747879A (en) | Large-process synthesis method of erexib | |
| CN110194760B (en) | Process for preparing 3-benzylidene-2- (7' -quinoline) -2, 3-dihydro-isoindol-1-ones | |
| Webster et al. | Tetracyano-p-phenylenediamine | |
| WO2020051853A1 (en) | 3,3-disubstituted oxindole and preparation method thereof | |
| CN108530445A (en) | A kind of synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound | |
| CN114805209B (en) | Preparation method of visible light-induced 3-aryl-2H-indazole compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |