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A kind of synthetic method of heteroatom-directed synthesis of benzoquinoline ester derivatives

A technology of benzoquinoline and synthetic method, which is applied in the direction of organic chemistry, can solve the problems of not being suitable for industrial production, many side reactions, and high cost, and achieve the effects of low cost, few side reactions, and cost saving

Active Publication Date: 2021-09-28
ANHUI NORMAL UNIV
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Problems solved by technology

[0005] In summary, there are many methods for synthesizing benzobenzoquinoline ester derivatives in the prior art, but some of these methods require complex synthesis steps and have many side reactions and relatively low yields; some use highly toxic Substrates or organic solvents are easy to cause environmental pollution; some use precious metal palladium as catalysts, which are relatively expensive and not suitable for industrial production.

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  • A kind of synthetic method of heteroatom-directed synthesis of benzoquinoline ester derivatives
  • A kind of synthetic method of heteroatom-directed synthesis of benzoquinoline ester derivatives
  • A kind of synthetic method of heteroatom-directed synthesis of benzoquinoline ester derivatives

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[0029] The invention provides a heteroatom-directed synthesis method for benzoquinoline ester derivatives, which comprises: heating and reacting quinoline derivatives, an organic carboxylic acid, a copper catalyst and a silver salt in an organic solvent under mixed conditions , to obtain benzoquinoline ester derivatives; wherein the quinoline derivatives are benzoquinoline as shown in formula I or 2-phenoxypyridine as shown in formula II; the benzoquinoline esters The structural formula of the derivative is shown in formula III or formula IV, X is the ester group in the organic carboxylic acid;

[0030]

[0031] Through the above technical scheme, the present invention overcomes many defects in the synthesis of quinoline ester derivatives in the prior art, and provides a synthetic method for synthesizing benzoquinoline ester derivatives, using silver salt as an oxidant, cheap Copper catalysts such as (one or more of copper acetate, copper sulfate, cuprous bromide, cuprous o...

Embodiment 1

[0046] The synthesis of 10-benzoquinoline benzoate comprises the following steps:

[0047] A. Take 0.2mmol benzoquinoline and 0.3mmol benzoic acid in the reaction tube, then add 0.04mmol Cu in turn 2 O, 0.4 mmol Ag 2 CO 3 , 3mL PhCl, stirred and reacted at 140°C for 18h.

[0048] B. Extract the product with ethyl acetate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography (volume ratio of solvent: petroleum ether: ethyl acetate = 10:1) A white solid was obtained. The result is as Figure 2a , Figure 2b As shown, it was confirmed to be 10-benzoquinoline benzoate. Yield 91%.

[0049] 1 H NMR (300MHz, CDCl 3 ): δ8.38(d, J=7.2Hz, 3H), 8.09(d, J=7.8Hz, 1H), 7.86(t, J=9.0Hz, 2H), 7.75-7.65(m, 3H), 7.60 -7.51(m,3H),7.36-7.32(m,1H). 13 C NMR (75MHz, CDCl 3 ): δ166.7, 148.8, 147.6, 145.3, 135.8, 135.2, 132.5, 131.1, 130.2, 128.1, 127.9, 127.7, 126.8, 126.4, 126.1, 123.1,...

Embodiment 2

[0052] The synthesis of 10-benzoquinoline-4-chlorobenzoate comprises the following steps:

[0053] A. Take 0.2mmol benzoquinoline and 0.3mmol 4-chlorobenzoic acid in the reaction tube, then add 0.04mmol Cu in turn 2 O, 0.4 mmol Ag 2 CO 3 , 3mL PhCl, stirred and reacted at 140°C for 18h.

[0054] B. Extract the product with ethyl acetate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography (volume ratio of solvent: petroleum ether: ethyl acetate = 10:1) A yellow solid was obtained. The result is as Figure 3a , Figure 3b As shown, it was confirmed to be 10-benzoquinoline-4-chlorobenzoate.

[0055] Yield 87%

[0056] 1 H NMR (500MHz, CDCl3): δ8.38 (dd, J = 4.5, 2.0Hz, 1H), 8.31 (d, J = 8.5Hz, 2H), 8.11 (dd, J = 8.0, 2.0Hz, 1H), 7.90-7.84(m,2H),7.75-7.69(m,2H),7.56-7.50(m,3H),7.36(q,J=4.5Hz,1H). 13 C NMR (125MHz, CDCl3): δ166.7, 149.5, 148.5, 146.1, 139.8, 136.7, 136....

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Abstract

The invention discloses a heteroatom-directed synthesis method of benzoquinoline ester derivatives, which comprises: heating and reacting quinoline derivatives, organic carboxylic acids, copper catalysts and silver salts in an organic solvent under mixed conditions , to obtain benzoquinoline ester derivatives; wherein the quinoline derivatives are benzoquinoline as shown in formula I or 2-phenoxypyridine as shown in formula II; the benzoquinoline esters The structural formula of the derivative is shown in formula III or formula IV, and X is the ester group in the described organic carboxylic acid; This method is carried out in air atmosphere, and cost is low, does not need to use highly toxic substrate or organic solvent, does not need Precious catalysts such as precious metal palladium, the raw materials in the present invention are easy to obtain, the synthesis steps are simple, the side reactions are few, the yield of the target product is high, and the promotion value is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method for heteroatom-directed synthesis of benzoquinoline ester derivatives. Background technique [0002] Benzoquinoline (BQ) is a nitrogen-containing polycyclic aromatic hydrocarbon. Since one carbon atom in the aromatic ring structure is replaced by a nitrogen atom, it is also called monoazaphenanthrene. Among them, compounds containing benzoquinoline skeletons exist in many natural products and drugs with biological activity. Drugs containing BQ often have the effects of anti-tumor, anti-inflammatory and antibacterial, and treatment of malaria. Because of its important application value in the fields of production and medicine, the research on its synthesis method is particularly important. [0003] The method of the synthetic benzoquinoline ester compound of report in the literature mainly contains following several kinds: [0004] (1) In 2007, Sa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/10C07D409/12C07D213/643
CPCC07D213/643C07D221/10C07D409/12
Inventor 张武舒超
Owner ANHUI NORMAL UNIV
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