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Arylquinoline derivative synthesis method

An arylquinoline and a synthesis method technology, applied in the direction of organic chemistry and the like, can solve the problems of not conforming to the development of green chemistry, harsh reaction temperature and conditions, low atom utilization rate, etc., achieving easy commercial purchase or preparation, convenient operation, The effect of improved substrate availability

Inactive Publication Date: 2019-11-19
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires higher temperatures and requires the use of toxic CCl 4 As a solvent, not only the yield is not high, but also does not meet the needs of the development of green chemistry
Document (Org.Biomol.Chem.2017,15,1334) reported the palladium-catalyzed cyclization reaction of 2-vinylaniline derivatives and dimethyl sulfoxide to prepare aryl quinoline derivatives, although this method does not require cumbersome additives, but the reaction temperature and conditions are harsh, and it can only be carried out smoothly under a nitrogen atmosphere at 130°C, and the utilization rate of atoms is not high, and raw materials are rare

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of 2-phenylquinoline, structural formula is as follows:

[0027]

[0028] Under air atmosphere, add raw material (E)-3-(2-aminobenzene)acrylonitrile (0.3mmol), phenylboronic acid (0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-toluenesulfonic acid monohydrate Compound (0.6mmol), toluene (2mL), reacted at 90°C for 36h, and the isolated yield of the product was 90%. 1 H NMR (500MHz, CDCl 3 )δ8.24-8.17(m,4H),7.89(d,J=11.0Hz,1H),7.84(d,J=10.0Hz,1H),7.76-7.72(m,1H),7.56-7.52(m ,3H),7.49-7.46(m,1H); 13 C NMR (125MHz, CDCl 3 )δ157.4, 148.3, 139.6, 136.8, 129.7, 129.6, 129.4, 128.8, 127.6, 127.4, 127.2, 126.3, 119.0.

Embodiment 2

[0030] The preparation of 2-(4-methylphenyl) quinoline, structural formula is as follows:

[0031]

[0032] Under air atmosphere, add raw material (E)-3-(2-anilino)acrylonitrile (0.3mmol), 4-methylphenylboronic acid (0.6mmol) and catalyst palladium trifluoroacetate (5mol%), p-toluene Sulfonic acid monohydrate (0.6mmol), toluene (2mL), reacted at 90°C for 36h, and the isolated yield of the product was 88%. 1 H NMR (500MHz, CDCl3) δ8.19-8.07(m, 4H), 7.87-7.81(m, 2H), 7.72-7.71(m, 1H), 7.51-7.48(m, 1H), 7.34-7.33(m ,2H),2.43(s,3H); 13 C NMR (125MHz, CDCl3) δ157.3, 148.2, 139.5, 136.8, 136.7, 129.7, 129.6, 129.5, 127.4, 127.1, 126.1, 118.9, 21.3.

Embodiment 3

[0034] The preparation of 2-(3,5-dimethylphenyl) quinoline, the structural formula is as follows:

[0035]

[0036] Under air atmosphere, add raw materials (E)-3-(2-anilino)acrylonitrile (0.3mmol), p-toluenesulfonic acid monohydrate (0.6mmol), 3,5-dimethylphenylboronic acid (0.6 mmol) and catalyst palladium trifluoroacetate (5mol%), toluene (2mL), reacted at 90°C for 36h, and the isolated yield of the product was 88%. 1 H NMR (500MHz, CDCl 3 )δ8.20(t, J=7.5Hz, 2H), 7.86(d, J=8.5Hz, 1H), 7.82(d, J=8.5Hz, 1H), 7.78(s, 2H), 7.75-7.72( m,1H),7.52(t,J=7.5Hz,1H),7.12(s,1H),2.45(s,6H); 13 C NMR (125MHz, CDCl 3 )δ157.8, 148.3, 139.7, 138.4, 136.6, 131.1, 129.7, 129.6, 127.5, 127.2, 126.2, 125.5, 119.3, 21.5.

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis, and specifically relates to an arylquinoline derivative synthesis method, wherein the synthesis of arylquinoline derivatives with diversified structures is achieved through palladium-catalyzed continuous carbon-carbon / carbon-nitrogen bond construction, and specifically a 2-arylquinoline derivative is prepared by using a compound (E)-3-(2-aniline)acrylonitrile and arylboronic acid as raw materials under a palladium catalyst system. According to the present invention, the method has characteristics of wide raw material source oreasy preparation, simple operation, controllable selectivity, high yield, mild conditions and wide applicability.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of aryl quinoline derivatives which can realize structural diversification by building continuous carbon-carbon / carbon-nitrogen bonds. Background technique [0002] The quinoline skeleton widely exists in biologically active molecules and is one of the most representative heterocyclic compounds in medicine and pesticides, and it also plays an important role in the field of functional materials. Among the existing technologies for preparing quinoline, the traditional technology mainly utilizes the condensation reaction of aniline under the action of acid, base, and suitable coupling reagents, such as Knorr, Friedlander, and Skraup reactions. These methods are inconvenient to operate, require high equipment costs, and have a narrow scope of substrate application. The literature (J.Org.Chem.2012,48,690-693 and Heterocyclic Chem.2016,53,1022-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/04C07D215/12C07D215/18C07D409/04
CPCC07D215/04C07D215/12C07D215/18C07D409/04
Inventor 邵银林陈久喜许彤叶鹏清戴玲徐北航孙佳妮
Owner WENZHOU UNIVERSITY
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