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Synthesis method of 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound

A synthetic method, 3-c technology, applied in the direction of organic chemistry, etc., can solve the problems of complex reaction conditions and long reaction steps

Active Publication Date: 2021-08-06
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the above method for the synthesis of 7H-indole [2,3-c] quinoline compounds, most of the starting materials used involve halides, and there are long reaction steps, complex reaction conditions and other shortcomings, further development in mild conditions In this way, the green synthesis of 7H-indole[2,3-c]quinoline series compounds can be realized by means of C-H bond activation, etc., which has high research value

Method used

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  • Synthesis method of 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound
  • Synthesis method of 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound
  • Synthesis method of 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 6-phenyl-7-(pyridin-2-yl)-7H-indolo[2,3-c]quinoline

[0023] 6-phenyl-7-(pyridin-2-yl)-7H-indolo[2,3-c]quinoline

[0024]

[0025] In the dried Schlenk tube, add successively: 1-(pyridin-2-yl)-1H-indole (0.2mmol, 38.8mg), (Z)-N,1-diphenylmethanimine Oxide (0.4mmol, 78.8mg), acetic acid (0.4mmol, 24.0mg), [Cp*IrCl 2 ] (5.0 mol%) and 2 mL of hexafluoroisopropanol. And the above-mentioned Schlenk tube was placed under the condition of 80° C., and the reaction time was 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and washed with CH 2 Cl 2 (10mL) and dilute with CH 2 Cl 2 (2 x 10 mL) was passed through a short pad of celite and the solvent was removed on a rotary evaporator. Finally, it was separated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1), and the yield was 88% (65.4 mg). The compound was a yellow solid.

[0026] NMR data: 1 H NMR (CDCl 3 ,400MHz):δ...

Embodiment 2

[0027] Example 2 6-phenyl-7-(pyridin-2-yl)-7H-indolo[2,3-c]quinoline

[0028] 6-phenyl-7-(pyridin-2-yl)-7H-indolo[2,3-c]quinoline

[0029]

[0030] In the dried Schlenk tube, add successively: 1-(pyridin-2-yl)-1H-indole (0.2mmol, 38.8mg), (Z)-N,1-diphenylmethanimine Oxide (0.4mmol, 78.8mg), acetic acid (0.4mmol, 24.0mg), [Cp*RhCl 2 ] (5.0 mol%) and 2 mL of hexafluoroisopropanol. And the above-mentioned Schlenk tube was placed under the condition of 80° C., and the reaction time was 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and washed with CH 2 Cl 2 (10mL) and dilute with CH 2 Cl 2 (2 x 10 mL) was passed through a short pad of celite and the solvent was removed on a rotary evaporator. Finally, it was separated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=3:1) with a yield of 40% (29.7 mg). The compound was a yellow solid.

[0031] NMR data: 1 H NMR (CDCl 3,400MHz):δ8.88...

Embodiment 3

[0032] Example 3: 7-(6-methylpyridin-2-yl)-6-phenyl-7H-indolo[2,3-c]quinoline

[0033] 7-(6-methylpyridin-2-yl)-6-phenyl-7H-indolo[2,3-c]quinoline

[0034]

[0035] In the dried Schlenk tube, add 1-(6-methylpyridin-2-yl)-1H-indole (0.2mmol, 41.4mg), (Z)-N,1-diphenyl Formimine oxide (78.8mg, 0.4mmol), acetic acid (0.4mmol, 24.0mg), [Cp*IrCl 2 ] (5.0 mol%) and 2 mL of hexafluoroisopropanol. And the above-mentioned Schlenk tube was placed under the condition of 80° C., and the reaction time was 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and washed with CH 2 Cl 2 (10mL) and dilute with CH 2 Cl 2 (2 x 10 mL) was passed through a short pad of celite and the solvent was removed on a rotary evaporator. Finally, it was separated and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=5:1) with a yield of 41% (31.5 mg). The compound was a yellow solid.

[0036] NMR data: 1 H NMR (CDCl 3 ,40...

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Abstract

The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a synthesis method of a 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound. The method comprises the following steps: by taking indolpyridine and nitrone as raw materials, iridium or ruthenium as a catalyst and alcohol as a solvent in the presence of acid, carrying out a heating reaction at 50-100 DEG C for 20-30 hours to synthesize a product. And a series of 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compounds with high yield can be obtained through simple post-treatment in the reaction. The 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound can be used as a raw material, indole pyridine with various substituent groups and nitrone with various substituent groups can be used as reaction substrates, and the corresponding 6-phenyl-7-(pyridine-2-yl)-7H-indolo [2, 3-c] quinoline compound is obtained.

Description

technical field [0001] The present invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a simple and efficient synthesis of 6-phenylene compound catalyzed by iridium or ruthenium, using indolepyridine and nitrone as raw materials, with the participation of acid and alcohol as a solvent -7-(pyridin-2-yl)-7H-indolo[2,3-c]quinoline compound method. Background technique [0002] Indolequinoline alkaloids, such as: cryptolepine (cryptolepine), neocryptolepine (neocryptolepine), isocryptolepine (isocryptolepine), etc., are widely present in plants such as cryptolepine, and have good In addition, it also has pharmacological activities such as anti-tumor cells, anti-fungal, anti-microbial, anti-bacterial, and anti-inflammatory. Isoneocryptolepine (indole [2,3-c] quinoline) is another important class of indole quinoline derivatives, which has good anti-plasmodium activity. This type of compound has not been extracted fro...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 孙松李渺董亚群孙建伟周聪
Owner CHANGZHOU UNIV
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