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Synthetic Technology of 3-Nitroquinoline Derivatives

A synthesis process and nitroquinoline technology, applied in directions such as organic chemistry, can solve the problems of complicated post-processing, cumbersome preparation, few synthesis methods, etc., and achieve the effects of simple post-processing, high reaction yield, and low-cost catalyst.

Active Publication Date: 2021-01-05
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

[0004] Yet so far, the synthetic method of 3-nitroquinoline compound is very little, mainly contains following three kinds: (1) directly carry out nitration to quinoline ring, there is not high selectivity, generate the isomer of several positions , and will oxidize the quinoline ring to form the nitrogen oxide of quinoline, so the direct nitration method is rarely used in the synthesis of 3-nitroquinoline compounds
(2) Use 2-aminobenzaldehyde and α-nitroketones to condense in alcohol solvents to obtain 3-nitroquinoline, but the preparation of this ketones is cumbersome and the substrate has strong limitations sex
This method is widely used, but there are three problems. One is that the first step cycloaddition process needs to use toxic benzene as a solvent, and the other is that anthranilaldehyde is very easy to polymerize, which is very expensive and practical will lead to low yield, and the third is that the reaction needs to be carried out in two steps, and multiple equivalents of alkali and oxidant are used, and the post-treatment is complicated

Method used

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  • Synthetic Technology of 3-Nitroquinoline Derivatives
  • Synthetic Technology of 3-Nitroquinoline Derivatives
  • Synthetic Technology of 3-Nitroquinoline Derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The specific steps are: add nitrostyrene (1mmol), 2-azidobenzaldehyde (1.5mmol), CuI (0.01mmol), DMF (2mL) to a round bottom flask (50mL), and react with magnetic stirring at 110°C After 8 hours, after dissolving with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was prepared with ethyl acetate / petroleum ether=1:10 ( V / V) is the eluent and subjected to column separation and purification to obtain the desired product 2-phenyl-3-nitroquinoline as a yellow solid with a yield of 85%.

[0037] like figure 1 and figure 2 , the proton nuclear magnetic spectrum result of gained product is: 1 H NMR (600MHz, DMSO-d 6 ):δ8.60(s,1H),8.20(d,J=8.4Hz,1H),7.90(d,J=8.4Hz,1H),7.86(t,J=7.8Hz,1H),7.63(t ,J=7.2Hz,1H),7.58(d,J=7.8Hz,2H),7.30(d,J=7.8Hz,2H),2.42(s,3H). 13 C NMR (100MHz, CDCl 3 , ppm) δ152.1, 148.3, 143.9, 137.0, 132.8, 132.6, ...

Embodiment 2

[0039] The specific steps are: add nitro-o-bromostyrene (1mmol), 2-azidobenzaldehyde (1.5mmol), CuI (0.01mmol), toluene (2mL) to a round bottom flask (50mL), and magnetically After stirring and reacting for 12 hours, dissolve it with ethyl acetate, wash the organic layer with saturated brine, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain the crude product, and use ethyl acetate / petroleum ether=1 :10 (V / V) is the eluent and carries out column separation and purification to obtain the desired product 2-(2-bromophenyl)-3-nitroquinoline as a yellow solid with a yield of 78%.

[0040] like image 3 and Figure 4 , the proton nuclear magnetic spectrum result of gained product is: 1 H NMR (600MHz, CDCl 3 , ppm) δ8.98(s, 1H), 8.25(d, J=8.4Hz, 1H), 8.06(d, J=7.8Hz, 1H), 7.95(t, J=7.2Hz, 1H), 7.74( t,J=7.2Hz,1H),7.65(d,J=7.8Hz,1H),7.59-7.45(m,2H),7.34(t,J=7.2Hz,1H). 13 C NMR (100MHz, CDCl 3 , ppm) δ152.2, 148.5, 143.0, 139.4, 133.4, 133....

Embodiment 3

[0042] The specific steps are: add nitrostyrene (1mmol), 2-azido-4-fluorobenzaldehyde (1.5mmol), Cu 2 O (0.01mmol), DMSO (2mL), magnetically stirred at 100°C for 15 hours, dissolved in ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and distilled off the solvent under reduced pressure. Get the crude product, the crude product uses ethyl acetate / petroleum ether=1:15 (V / V) as the eluent to carry out column separation and purification to obtain the desired product 2-phenyl-3-nitro-7-fluoroquine phenoline, the product is a yellow solid, and the yield is 72%.

[0043] Such as Figure 5 with Image 6 , the proton nuclear magnetic spectrum result of gained product is: 1 H NMR (600MHz, CDCl 3 ,ppm)δ8.70(s,1H),8.03-7.97(m,1H),7.86(d,J=9.6Hz,1H),7.65(s,2H),7.48-7.51(m,4H). 13 C NMR (150MHz, CDCl 3 , ppm) δ166.0, 164.3, 153.3, 149.6 (d, J = 13.4Hz), 143.5, 136.7, 132.7, 130.8 (d, J = 10.4Hz), 129.8, 128.8, 122.5, 119.3 (d, J = 25.9...

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Abstract

The invention relates to a method for synthesizing 3-nitroquinoline derivatives. Nitroolefin and ortho-aldehyde-substituted aryl azide undergo a [3+2] cycloaddition reaction in the presence of a solvent under the action of a copper salt catalyst, wherein the nitroolefin is alkyl-, substituted alkyl-, aryl- or substituted aryl-substituted nitroolefin, and an aryl group in the ortho-aldehyde-substituted aryl azide is an aryl group or a substituted aryl group. The cheap and easily available ortho-aldehyde-substituted aryl azide used as a raw material and the nitroolefin undergo the [3+2] cycloaddition under the catalysis of the copper salt to obtain 3-nitroquinoline compounds, so the method has the advantages of high reaction yield, low price of the catalyst, and simplicity in post-treatmentof reaction byproducts only being nitrogen and water, and is an environmentally-friendly synthesis method.

Description

technical field [0001] The invention relates to a method for synthesizing 3-nitroquinoline derivatives, belonging to the technical field of organic and pharmaceutical synthesis. [0002] technical background [0003] Quinoline is an important class of nitrogen-containing heterocyclic compounds in organic synthesis. Among them, the quinoline substituted by the nitrogen atom at the 3rd position widely exists in natural products, such as quinoline alkaloids, which have good antimalarial and anticancer activities. In addition, some compounds containing this skeleton also have Anti-cancer, anti-malarial, anti-asthma, anti-diabetic, antibacterial, anti-tumor properties. As the precursors of these compounds, 3-nitroquinoline compounds have the characteristics of stable properties and easy derivatization. They have attracted much attention in organic synthesis and have considerable potential in drug synthesis. [0004] Yet so far, the synthetic method of 3-nitroquinoline compound i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/18C07D405/04C07D215/20
CPCC07D215/18C07D215/20C07D405/04
Inventor 陈云峰郑镭
Owner WUHAN INSTITUTE OF TECHNOLOGY
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