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Environment-friendly synthetic method of 4-ferrocenyl quinoline derivative

A ferrocene-based quinoline, derivative technology, applied in chemical instruments and methods, metallocene, organic chemistry and other directions, can solve the problems of non-conformity to green synthesis, low synthesis efficiency, heavy metal pollution, etc., and achieves low cost, green Effects of mild synthesis and reaction conditions

Active Publication Date: 2017-12-12
SHANDONG NORMAL UNIV
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AI Technical Summary

Problems solved by technology

However, the synthesis efficiency of these methods is low, especially the use of metal catalysts, not only the cost is high, but also easy to cause heavy metal pollution
In addition, the synthesis reaction uses toluene solvent, which is easy to cause environmental pollution and does not meet the requirements of green synthesis

Method used

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  • Environment-friendly synthetic method of 4-ferrocenyl quinoline derivative
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  • Environment-friendly synthetic method of 4-ferrocenyl quinoline derivative

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preparation example Construction

[0021] In view of this, the present invention provides a kind of green synthetic method of 4-ferrocenyl quinoline derivative, and this synthetic method comprises:

[0022] Using an organic acid as a catalyst, ferrocenyl acetylene, aromatic aldehyde and aromatic primary amine undergo a three-component cyclization reaction in a solvent to generate 4-ferrocenyl quinoline derivatives in one step; the organic acid is p-toluenesulfonic acid , trifluoromethanesulfonic acid, trifluoroacetic acid or acetic acid, the solvent is water, ethanol or methanol;

[0023] Wherein, the structural formula of the aromatic aldehyde is as follows:

[0024] Ar-CHO

[0025] The structural formula of the aromatic primary amine is as follows:

[0026]

[0027] The structural formula of the 4-ferrocenyl quinoline derivative is as follows:

[0028]

[0029] In the above structural formula, R is H, CH 3 、CH 3 O, OH, NO 2 , Cl or Br, R is located at the 5, 6, 7 or 8 position of the quinoline rin...

Embodiment 1

[0046] Synthesis of 2-phenyl-4-ferrocenylquinoline

[0047] A mixture of ferroceneacetylene (0.231g, 1.1mmol), benzaldehyde (0.106g, 1.0mmol), aniline (0.093g, 1.1mmol), p-toluenesulfonic acid (0.017g, 0.1mmol) and water (1mL) , and stirred the reaction at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, ethyl acetate was added, washed with saturated sodium bicarbonate solution and brine respectively, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography (silica gel: 200-300 mesh, eluent: ethyl acetate / petroleum ether=1:20, v / v, R f =0.3) to obtain a red solid with a yield of 90%, m.p.145-146°C. HR-MS: Calcd for C 25 h 19 FeN[M] + :390.0945,Found:390.0975; 1 H NMR (CDCl 3 ,300MHz):δ8.61(d,J=9.0Hz,1H,Ar-H),8.23-8.20(m,3H,Ar-H),8.16(s,1H,Ar-H),7.72(t, J=6.6Hz, 1H, Ar-H)...

Embodiment 2

[0049] Synthesis of 2-phenyl-4-ferrocenylquinoline

[0050] Ferroceneacetylene (0.231g, 1.1mmol), benzaldehyde (0.106g, 1.0mmol), aniline (0.093g, 1.1mmol), trifluoromethanesulfonic acid (0.015g, 0.10mmol) and ethanol (1mL) The mixture was stirred and reacted at 80°C for 2 hours. The reaction mixture was cooled to room temperature, ethyl acetate was added, washed with saturated sodium bicarbonate solution and brine respectively, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the filtrate under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography (silica gel: 200-300 mesh, eluent: ethyl acetate / petroleum ether=1:20, v / v, R f =0.3) to obtain a red solid with a yield of 95%. The structural characterization data are the same as in Example 1.

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Abstract

The invention discloses an environment-friendly synthetic method of a 4-ferrocenyl quinoline derivative. The method is prominently characterized in that ethynylferrocene, aromatic aldehyde and aromatic primary amine generate a three-component cyclization reaction in water under the catalysis of a small amount of organic acid, so as to efficiently synthesize the 4-ferrocenyl quinoline derivative in one step. Compared with the prior art, the environment-friendly synthetic method has the advantages that, heavy metal salt and toxic solvent toluene are not used, the inert gas shielding is not required, reaction conditions are mild, the yield is high, the cost is low, the environmental protection is realized, and the like. A new effective way is provided for rich and structurally diverse quinoline metal derivatives, and the method has wide application prospects.

Description

technical field [0001] The invention belongs to the field of synthesis of metal-organic heterocyclic compounds, and in particular relates to a green synthesis method of 4-ferrocenylquinoline derivatives. Background technique [0002] Quinoline is an important nitrogen-containing fused heterocyclic organic compound, and its derivatives have rich and diverse structures and a wide range of biological activities. There are quinoline heterocyclic skeletons in many natural products, medicines, pesticides and dyes and other chemical molecules. Especially in the field of new drug development, introducing quinoline rings into the molecular structure of some organic compounds often presents such as Antimicrobial, anti-malarial, anti-HIV, anti-tuberculosis, anti-tumor and other biological activities ((a) Heiniger, B.; Gakhar, G.; Prasain, K.; Hua, D.H.; Nguyen, T.A. Anticancer Res. 2010, 30 , 3927.(b) Teguh, S.C.; Klonis, N.; Duffy, S.; Lucantoni, L.; Avery, V.M., Hutton, C.A.; Baell,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 郭佃顺牟瑞琪张圣燕张霞汪菊琴
Owner SHANDONG NORMAL UNIV
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