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Carbazole indolequinone derivative as well as preparation method and application thereof

A technology of carbazole indole quinone and its derivatives, which is applied in the field of carbazole indole quinone derivatives and its preparation, can solve problems affecting industrial production, harsh reaction conditions, and low product yield, and achieve good fluorescence characteristics, The effect of simple operation and easy-to-obtain raw materials

Pending Publication Date: 2020-07-31
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing synthetic methods have the following problems to varying degrees: such as the preparation of essential functional groups, multiple reaction steps, harsh reaction conditions, expensive catalysts, and low product yields due to side reactions, which have seriously affected the industry. chemical production

Method used

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  • Carbazole indolequinone derivative as well as preparation method and application thereof
  • Carbazole indolequinone derivative as well as preparation method and application thereof
  • Carbazole indolequinone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] Add nitrogen methyl indole naphthoquinone compound (86.2mg, 0.3mmol), aniline (41.9mg, 0.45mmol), CoCl 2(1.2mg, 0.009mmol), t-BuOK (50.5mg, 0.45mmol) and DMF (2mL), mix well. Then, it was stirred at 120° C. for 24 h under an air atmosphere. After the reaction was complete (monitored by TLC), it was cooled to room temperature. The reaction was quenched with saturated brine (5 ml), and the mixture was extracted with EtOAc (3 x 5 mL). Then the aqueous layer was extracted with ethyl acetate, the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA=5:1) to obtain a red solid 3aa with a yield of 89%.

[0040] The melting point is 274-276°C. 1H NMR (400MHz, CDCl 3 )δ8.35(d, J=7.3Hz, 1H), 8.14(d, J=5.9Hz, 1H), 7.94(d, J=5.5Hz, 1H), 7.60(d, J=15.9Hz, 7H) ,7.36–7.23(m,3H),7.17(d,J=7.6Hz,1H),3.24(s,3H).13C NMR(101MHz,CDCl 3 )δ181.88, 174.08, 143.50, 136.44, 134.64, 133.08, 132....

Embodiment 2

[0042]

[0043] Add nitrogen methyl indole naphthoquinone compound (86.2mg, 0.3mmol), p-methylaniline (48.2mg, 0.45mmol), CoCl 2 (1.2mg, 0.009mmol), t-BuOK (50.5mg, 0.45mmol) and DMF (2mL), mix well. Then, it was stirred at 120° C. for 24 h under an air atmosphere. After the reaction was complete (monitored by TLC), it was cooled to room temperature. The reaction was quenched with saturated brine (5 ml), and the mixture was extracted with EtOAc (3 x 5 mL). Then the aqueous layer was extracted with ethyl acetate, the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA=5:1) to obtain a red solid 3ab with a yield of 85%.

[0044] The melting point is 275-277°C. 1H NMR (400MHz, CDCl 3 )δ8.36(d,J=7.2Hz,1H),8.16(s,1H),7.97(s,1H),7.59(s,2H),7.46(s,2H),7.41(s,2H), 7.33–7.27(m,2H),7.20(d,J=7.5Hz,1H),3.28(s,3H),2.51(s,3H).13C NMR(101MHz,CDCl 3 )δ181.92,174.12,143.54,139.93,134.73,133.76,133....

Embodiment 3

[0046]

[0047] Add nitrogen methyl indole naphthoquinone compound (86.2mg, 0.3mmol), p-methoxyaniline (55.4mg, 0.45mmol), CoCl 2 (1.2mg, 0.009mmol), t-BuOK (50.5mg, 0.45mmol) and DMF (2mL), mix well. Then, it was stirred at 120° C. for 24 h under an air atmosphere. After the reaction was complete (monitored by TLC), it was cooled to room temperature. The reaction was quenched with saturated brine (5 ml), and the mixture was extracted with EtOAc (3 x 5 mL). Then the aqueous layer was extracted with ethyl acetate, and the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA=5:1) to obtain a red solid 3ac with a yield of 81%.

[0048] The melting point is 266-268°C. 1H NMR (400MHz, CDCl 3 )δ8.34(d, J=7.1Hz, 1H), 8.15(s, 1H), 7.95(s, 1H), 7.58(s, 2H), 7.51(d, J=7.5Hz, 2H), 7.35– 7.26(m,2H),7.17(d,J=7.5Hz,1H),7.10(d,J=7.6Hz,2H),3.93(s,3H),3.28(s,3H).13C NMR(101MHz, CDCl 3 )δ181.88, 174...

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Abstract

The invention discloses a carbazole indolequinone derivative, which is a compound with a brand new structure and has good fluorescence characteristic and medicinal value. The invention further provides a preparation method of the carbazole indolequinone derivative. The derivative is synthesized from an indolequinone compound and aromatic amine in one step under the action of a solvent, a catalystand an alkali. The raw materials are easy to obtain, the operation is simple, the synthesis is convenient and rapid, and the industrial production is easy to realize. The invention also provides an application of the carbazole indolequinone derivative, and the carbazole indolequinone derivative is used as a fluorescent material or a medicinal material to be applied to various fields and has a goodapplication prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a carbazole indole quinone derivative and its preparation method and application. Background technique [0002] N-heterocyclic compounds widely exist in nature and are important structural units of natural products, pharmaceutical molecules, and functional materials. [0003] There are many kinds of N-heterocyclic compounds, carbazoles are one of the nitrogen heterocyclic compounds, carbazoles include simple substituted carbazoles and cyclized polycyclic complex molecules, carbazoles are widely found in the genus Murata Studies have shown that these alkaloids have various biological activities such as antibacterial, anti-inflammatory, anti-oxidation, anti-cancer and anti-senile dementia. [0004] Among many carbazole alkaloids, carbazole quinone has two pharmacophore groups, indole and quinone, so that it exhibits a wide range of biological activities. At p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06A61P31/00A61P29/00A61P39/06A61P35/00A61P25/28
CPCC07D487/04C09K11/06A61P31/00A61P29/00A61P39/06A61P35/00A61P25/28C09K2211/1011C09K2211/1044C09K2211/1029
Inventor 王继宇董宇
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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