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8-hydroxyquinoline type compounds and preparation method thereof

A hydroxyquinoline and compound technology, which is applied in the field of 8-hydroxyquinoline compounds and their preparation, can solve the problems of high corrosiveness of chlorine-containing organic substances, high toxicity of o-chloroaniline, environmental pollution by tar, etc., and is conducive to rapid construction , The effect of low catalyst dosage and high yield

Active Publication Date: 2018-11-09
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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Problems solved by technology

[0004] But these methods have the following problems, method (1): a large amount of acid-base is needed in the sulfonated alkali fusion process, and the amount of waste water is large, and the environment is seriously polluted; method (2): the required raw material 8-chloroquinoline is made of o-chloroaniline Obtained, but the toxicity of o-chloroaniline is relatively large, and the corrosiveness of alkali hydrolysis of chlorinated organic matter is also very large; method (3): the required raw material 8-aminoquinoline is reduced by 8-nitroquinoline, but the quinoline Two isomers of 5-nitroquinoline and 8-nitroquinoline are obtained in the mixed acid nitration process and are difficult to separate; method (4): use o-aminophenol, concentrated sulfuric acid, glycerol and o-nitrophenol to obtain 8 - Hydroxyquinoline, this method needs to be carried out at high temperature, and the pyrolysis of glycerol produces tar to pollute the environment

Method used

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  • 8-hydroxyquinoline type compounds and preparation method thereof
  • 8-hydroxyquinoline type compounds and preparation method thereof
  • 8-hydroxyquinoline type compounds and preparation method thereof

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Experimental program
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Effect test

Embodiment 8

[0029] The synthetic method of present embodiment 8-hydroxyquinoline compound 4a is as follows:

[0030]

[0031] Add o-aminophenol (1.1mmol), benzaldehyde (1mmol) and phenylacetylene (1.2mmol) successively to a solution of AgOTf (0.5mol%) in dichloroethane (4mL), stir at room temperature, then add trifluoroacetic acid (4mmol), the temperature was raised to 80°C for reaction. TLC monitored the reaction until it was complete. After adding 20 mL of dichloromethane, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (PE / EA=20:1 as the eluent), 280 mg of light yellow solid powder was obtained, with a yield of 94%.

[0032] 1 H NMR (600MHz, CDCl 3 )δ8.16-8.20 (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; 13 C NMR (150MHz, CDCl 3 )δ152.0, 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.

Embodiment 2

[0034] The synthetic method of present embodiment 8-hydroxyquinoline compound 4b is as follows:

[0035]

[0036] Add o-aminophenol (1.2mmol), p-tolualdehyde (1mmol) and phenylacetylene (1.3mmol) successively to the toluene (4mL) solution containing AgOTf (0.5mol%), after stirring at room temperature, add trifluoroacetic acid (3mmol), the temperature was raised to 80°C for reaction. Followed by TLC spotting until the reaction was complete, concentrated to remove toluene, added 20 mL of dichloromethane, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (PE / EA=20:1 as eluent) to obtain 286 mg of light yellow solid , yield 92%.

[0037] 1 H NMR (600MHz, CDCl 3 )δ8.09(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; 13 C NMR (150MHz, CDCl 3 )δ153.4, 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,...

Embodiment 3

[0039] The synthetic method of present embodiment 8-hydroxyquinoline compound 4c is as follows:

[0040]

[0041]Add o-aminophenol (1.1mmol), 2,4,6-trimethylbenzaldehyde (1mmol) and phenylacetylene (1.5mmol) successively to a solution of AgOTf (1mol%) in dioxane (4mL), room temperature After stirring evenly, trifluoroacetic acid (1 mmol) was added, and the temperature was raised to 110°C for reaction. Tracked by TLC until the reaction was complete, concentrated to remove dioxane, added 20mL of dichloromethane, washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (PE / EA=15:1 as eluent) to obtain light Yellow solid 298mg, yield 88%.

[0042] 1 H NMR (600MHz, CDCl 3 )δ7.55-7.58(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; 13 C NMR (150MHz, CDCl3) δ156.6, 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.

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Abstract

8-hydroxyquinoline type compounds and a preparation method thereof are disclosed. The general structure formula of the compounds is shown in the description, wherein R1 and R2 are each independently selected from alkanes, cycloalkanes, phenyl, substituted phenyl or heterocyclic aromatic hydrocarbons, and a substitute of the substituted phenyl is one or a combination of two or more selected from alkyl, alkoxy, hydroxyl, halogen and an ester group. The method includes reacting a uniformly mixed system of 2-aminophenol, an aldehyde, an acetylene, a catalyst and an organic solvent in an air atmosphere at 60-110 DEG C for 0.5-4 h; and subjecting a reaction solution after the reaction is finished to after-treatment to obtain a target product that is a 8-hydroxyquinoline type compound. A multi-component one-pot process is adopted, raw materials are simple in source and rapid to prepare, the dosage of the catalyst is low, and the environment cost is greatly reduced. The method is simple to operate, high in yield and wide in substrate universality, and establishment of a molecular library of the 8-hydroxyquinoline type compounds is completed and enriched.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an 8-hydroxyquinoline compound and a preparation method thereof. Background technique [0002] 8-Hydroxyquinoline compounds are important intermediates in organic synthesis and are widely used in chemistry, pharmacy and medicine. 8-hydroxyquinoline compounds, as metal ion chelating agents with excellent performance, have been widely used in metallurgical industry and analytical chemistry for metal element chemical analysis, extraction of metal ions, photometric analysis and metal anticorrosion; due to 8-hydroxyquinoline and Most of the derivatives are biologically active, and they are the raw materials for the synthesis of important drugs such as Kexilining and halogenated quinoline anti-amoeba drugs. They are also widely used in the field of pharmaceutical industry; 8-hydroxyquinoline is directly used as a disinfectant Agent, its halogenated derivatives, n...

Claims

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Application Information

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IPC IPC(8): C07D215/26C07D405/04
CPCC07D215/26C07D405/04
Inventor 余述燕吴敬新兰宏兵尹志刚杨许召
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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