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Synthesis method of benzoyl quinoline compound

A technology of benzoylquinoline and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of reduced practicality, and achieve the effect of simple synthesis of raw materials

Inactive Publication Date: 2022-03-29
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, in many cases, the above methods require the use of large quantities of strong oxidizing agents, expensive or highly toxic additives, noble metal catalysts, and high temperatures, which greatly reduces the practicability of these methods

Method used

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  • Synthesis method of benzoyl quinoline compound
  • Synthesis method of benzoyl quinoline compound
  • Synthesis method of benzoyl quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0033] Example 1: 4-Phenyl-2-benzoylquinoline

[0034]

[0035] Add 2-(1-styryl)aniline (39.1mg, 0.2mmol), phenylsulfide ylide (58.9mg, 0.3mmol), iron phthalocyanine (5.7mg, 0.01mmol), carbonic acid Sodium (21.2 mg, 0.2 mmol). The reaction mixture was placed under blue light and stirred for 18 hours under heating conditions, then taken out and cooled to room temperature, added an appropriate amount of dichloromethane to dissolve, and the reaction solution was transferred and filtered. After the filtrate was concentrated, it was directly separated by silica gel column chromatography. Using a mixture of petroleum ether and ethyl acetate with a volume ratio of 60:1 as the eluent, it was separated by column chromatography with a yield of 94%.

[0036] 1 H NMR (500MHz, CDCl 3):δ8.29-8.27(m,3H),8.06(s,1H),8.02(d,J=8.5Hz,1H),7.81-7.78(m,1H),7.66-7.52(m,9H). 13 C NMR (125MHz, CDCl 3 ): δ193.8, 154.3, 149.6, 147.4, 137.7, 136.2, 133.0, 131.5, 130.9, 129.8, 129.6, 128.6, 128.4, ...

example 2

[0037] Example 2: 4-Phenyl-2-benzoyl-6-methoxyquinoline

[0038] Add 4-methoxy-2-(1-styryl)aniline (45.1mg, 0.2mmol), phenylsulfide ylide (58.9mg, 0.3mmol), iron phthalocyanine (5.7mg , 0.01mmol), sodium carbonate (21.2mg, 0.2mmol). The reaction mixture was placed under blue light and stirred for 18 hours under heating conditions, then taken out and cooled to room temperature, added an appropriate amount of dichloromethane to dissolve, and the reaction solution was transferred and filtered. After the filtrate was concentrated, it was directly separated by silica gel column chromatography. Using a mixture of petroleum ether and ethyl acetate with a volume ratio of 60:1 as the eluent, it was separated by column chromatography with a yield of 97%.

[0039] 1 H NMR (500MHz, CDCl 3 ): δ8.27(d, J=8.0Hz, 2H), 8.16(d, J=9.5Hz, 1H), 8.06(s, 1H), 7.64-7.51(m, 8H), 7.44(dd, J= 9.0,2.5Hz,1H),7.27(d,J=2.5Hz,1H),3.83(s,3H). 13 C NMR (125MHz, CDCl 3 ): δ193.8, 159.5, 152.0, 147.9, 143....

example 3

[0040] Example 3: 4-Phenyl-6-methyl-2-benzoylquinoline

[0041]

[0042] Add 4-methyl-2-(1-styryl)aniline (41.9mg, 0.2mmol), phenylsulfide ylide (58.9mg, 0.3mmol), iron phthalocyanine (5.7mg, 0.01 mmol), sodium carbonate (21.2 mg, 0.2 mmol). The reaction mixture was placed under blue light and stirred for 18 hours under heating conditions, then taken out and cooled to room temperature, added an appropriate amount of dichloromethane to dissolve, and the reaction solution was transferred and filtered. After the filtrate was concentrated, it was directly separated by silica gel column chromatography. Using a mixture of petroleum ether and ethyl acetate with a volume ratio of 60:1 as the eluent, it was separated by column chromatography with a yield of 91%.

[0043] 1 H NMR (500MHz, CDCl 3 ):δ8.28(d, J=8.0Hz, 2H), 8.17(d, J=8.5Hz, 1H), 8.04(s, 1H), 7.76(s, 1H), 7.65-7.51(m, 9H) ,2.52(s,3H). 13 C NMR (125MHz, CDCl 3 ): δ193.9, 153.4, 148.8, 145.9, 138.8, 137.9, 136.3, 132....

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Abstract

The invention discloses a synthesis method of a benzoyl quinoline compound, which comprises the step of carrying out dehydrocyclization reaction by using sodium carbonate as an accelerant under the condition of no solvent. According to the method, the 2-(1-styryl) aniline compound and sulfur ylide serve as raw materials, efficient and wide synthesis of the benzoyl quinoline compound is achieved under the mild condition, the used accelerant is sodium carbonate which is low in price and easy to obtain, raw material synthesis is simple, and compared with the prior art, the method has the higher practical application value and is suitable for industrial production. And popularization and application can be realized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically refers to a method for synthesizing benzoylquinoline compounds. Background technique [0002] Quinoline is one of the ubiquitous structural units in natural products and pharmaceutical active substances. Quinoline derivatives are widely used in medicinal chemistry, especially in anti-virus, anti-cancer, anti-tuberculosis and anti-malarial. Among them, the benzoylquinoline compound has anti-malarial activity, and can also treat AIDS together with other drugs. [0003] In the existing research on the synthesis of carbonyl quinoline compounds, the most commonly used method is to utilize the Povarov reaction. For example: et al. (Org. Lett. 2011, 13, 6066–6069) reported that α-aminocarbonyl compounds and alkenyl compounds were 3 A series of carbonyl ester quinoline compounds were synthesized under the condition of catalyst, and the reaction yield was moderate; 3 As an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/14C07D215/20C07D215/26C07D405/06
CPCC07D215/14C07D215/20C07D215/26C07D405/06
Inventor 余小春刘璐瑶金辉乐王舜
Owner WENZHOU UNIVERSITY