Nitro-substituted indole compound and preparation method thereof

A compound and indole technology, applied in the field of organic chemistry and medicinal chemistry, can solve the problems of low total yield and efficiency, difficult one-step synthesis, etc., achieve high product yield, easy post-processing, and avoid residue effects

Active Publication Date: 2020-01-21
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nitroindole compounds, because of the strong electron-withdrawing group nitro group attached to the indole skeleton, are difficult to synthesize in one step by classical methods and modern catalytic methods, and often need to be synthesized step by step, and the overall yield and efficiency are extremely low

Method used

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  • Nitro-substituted indole compound and preparation method thereof
  • Nitro-substituted indole compound and preparation method thereof
  • Nitro-substituted indole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Synthesis of 2,2-dimethyl-7-nitro-9-phenyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

[0039] (1) Weigh 0.3mmol of 1,3-dinitrobenzene (0.0504 grams), 0.45mmol of 5,5-dimethyl-3-(phenylamino)cyclohexyl-2-enyl-1-ketone (0.0969 grams), 0.75 mmol of cesium carbonate (0.2444 grams), in a 10 mL test tube reaction tube, add 2 mL of m-dichlorobenzene (MCB) as a solvent, seal and seal, and stir and react at 110 ° C for 12 hours;

[0040] (2) After the reaction finishes, the reaction solution is successively dried by water, ethyl acetate, anhydrous sodium sulfate and separated by column chromatography (column chromatography separation condition: the stationary phase is 300~400 mesh silica gel powder, and the mobile phase is ethyl acetate Ester (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:6→1:3, and 0.0622 g of the reaction product is obtained.

[0041] The above-mentioned reaction product is characterized, and the result is:

[0042] Colorless li...

Embodiment 2

[0044] Example 2 Synthesis of 2,2-dimethyl-7-nitro-9-(4-methylphenyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one

[0045] (1) Weigh 0.3mmol of 1,3-dinitrobenzene (0.0504 grams), 0.45mmol of 5,5-dimethyl-3-(4-methylphenylamino)cyclohexyl-2-enyl -1-ketone (0.1012 grams), 0.75 mmol of cesium carbonate (0.2444 grams), in a 10 mL test tube reaction tube, add 2 mL of m-dichlorobenzene (MCB) as a solvent, seal and seal, and stir at 110 ° C for 16 hours;

[0046] (2) After the reaction is over, the reaction solution is successively dried by water, ethyl acetate, anhydrous sodium sulfate and separated by column chromatography (column chromatography separation condition: the stationary phase is 300~400 mesh silica gel powder, and the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:6→1:3, and 0.0710 g of the reaction product is obtained.

[0047] The above-mentioned reaction product is characterized, and the result is:

[0048] Colorless ...

Embodiment 3

[0050] Example 3 Synthesis of 2,2-dimethyl-7-nitro-9-(4-methoxyphenyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one

[0051] (1) Weigh 0.3mmol of 1,3-dinitrobenzene (0.0504 grams), 0.45mmol of 5,5-dimethyl-3-(4-methoxyphenylamino)cyclohexyl-2-ene Base-1-ketone (0.1104 g), 0.75 mmol of cesium carbonate (0.2444 g), in a 10 mL test tube reaction tube, add 2 mL of m-dichlorobenzene (MCB) as a solvent, seal it tightly, and stir at 110 ° C for 17 hours ;

[0052] (2) After the reaction is over, the reaction solution is successively dried by water, ethyl acetate, anhydrous sodium sulfate and separated by column chromatography (column chromatography separation condition: the stationary phase is 300~400 mesh silica gel powder, and the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:6→1:3, and 0.885 g of the reaction product is obtained.

[0053] The above-mentioned reaction product is characterized, and the result is:

[0054] colorless ...

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Abstract

The invention discloses a preparation method of a nitro-substituted indole compound. The method comprises the following steps: mixing a dinitrobenzene compound and an enaminone compound according to amolar ratio of (1-3): (1-3); carrying out a stirring reaction on the mixture in an air atmosphere at a temperature of 25-150 DEG C in the presence of m-dichlorobenzene (MCB) as a solvent and an alkali promoter for 12-24 h; carrying out TLC detection to determine the reaction process, and after the reaction is finished, washing the reaction solution with water, extracting, drying and carrying outcolumn chromatography separation to obtain a target product. The method provided by the invention has the advantages of cheap and easily available raw materials, simple and mild catalytic conditions,convenient post-treatment, a high yield and the like, and the obtained product has good economic added value and certain economic benefits.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry, and in particular relates to a nitro-substituted indole compound and a synthesis method of the compound under the condition of no transition metal participation. Background technique [0002] The indole ring system is one of the most abundant and common heterocyclic compounds in nature. Indole compounds occupy an important position in the fields of biology, medicine and chemistry. A series of biologically active natural compounds, ranging from simple indole derivatives such as the neurotransmitter serotonin, to the clinically used anticancer drugs vincristine and mitomycin C, and the antihypertensive alkaloid reserpine contain Indole ring system skeleton. In addition, some commercially available synthetic drugs also contain indolyl sequences, including: sumatriptan, tadalafil, rizatriptan, fluvastatin, etc. [0003] The development of methods to synthesize diverse indo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 褚雪强葛丹华沈志良
Owner NANJING UNIV OF TECH
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