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Synthesis method of indole[2,3-b]carbazole compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of cumbersome post-processing, mild reaction conditions, restrictions, etc., and achieve the effect of wide range of use and simple operation.

Inactive Publication Date: 2018-01-30
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods all have problems such as mild reaction conditions, many by-products, cumbersome post-treatment, and limited scope of application, which greatly restrict the application of indole[2,3-b]carbazole and its derivatives.

Method used

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  • Synthesis method of indole[2,3-b]carbazole compound
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  • Synthesis method of indole[2,3-b]carbazole compound

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Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0019] A kind of synthetic method of indole [2,3-b] carbazole compound, synthetic process is:

[0020] Dissolve bis(2-indolyl)methane compound 1 and aromatic aldehyde compound 2 in a solvent, then add catalyst, stir at room temperature for 5 hours, filter directly after the reaction and wash with a small amount of ice ethanol to obtain indole [2,3-b]carbazole compound 3, the reaction equation is:

[0021]

[0022] where R 1 ,R 2 is hydrogen, but is not limited thereby; R 3 hydrogen, fluorine, chlorine, bromine, methyl, methoxy, dimethylamino, etc., but not limited thereto; the solvent is ethanol; the catalyst is oxalic acid; the reaction temperature is room temperature.

[0023] Further preferably, according to the amount ratio of substances, bis(2-indolyl)methane compound:aromatic aldehyde compound:catalyst=1:1:0.5.

Embodiment approach 2

[0025] A kind of synthetic method of indole [2,3-b] carbazole compound, synthetic process is: two (2-indolyl) methane compound 1 and terephthalaldehyde 4 are dissolved in the solvent, then add catalyst , stirred at room temperature for 5 hours, filtered directly after the reaction and washed with a small amount of ice ethanol to obtain indole[2,3-b]carbazole compound 5, the reaction equation is:

[0026]

[0027] where R 1 ,R 2 is hydrogen, but not so limited; the solvent is ethanol; the catalyst is oxalic acid; the reaction temperature is room temperature.

[0028] More preferably, according to the ratio of the amount of substances, bis(2-indolyl)methane compound:aromatic aldehyde compound:catalyst=2:1:0.5.

Embodiment 1

[0030]

[0031] In a 10 mL round bottom flask, bis(2-indolyl)methane (0.5 mmol, 123.0 mg) and oxalic acid (0.25 mmol, 22.5 mg) were dissolved in 5 mL of ethanol, then benzaldehyde 2a (0.5 mmol, 53 mg) was added , and stirred the reaction at room temperature for 5 hours. After the reaction was completed, it was filtered and washed with a small amount of ice ethanol to obtain a white solid 3a (157 mg, 94.5%). 1 H NMR (400MHz, DMSO-d 6 ):δ=11.10(s,2H),7.37-7.40(m,2H),7.32(d,J=4.0Hz,2H),7.17(d,J=4.0Hz,2H),6.97-7.02(m, 2H),6.81-6.85(m,2H),5.49(s,1H),4.17-4.42(m,2H); 13 C NMR (100MHz, DMSO-d 6 ): δ=142.94, 137.04, 131.74, 130.45, 126.54, 120.92, 118.73, 118.60, 115.22, 115.01, 112.17, 111.32, 38.16, 23.24; HRMS (ESI): [M+H + ]calcd.For[C 24 h 18 FN 2 ] + ,353.1454; found, 353.1454.

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Abstract

The invention provides a synthesis method of an indole[2,3-b]carbazole compound and belongs to the technical field of organic chemistry. The synthesis method comprises the following steps: 1) dissolving a di(2-indolyl)methane compound and an aromatic aldehyde compound into a solvent; 2) adding a catalyst and stirring to react at a room-temperature condition; 3) after reacting, filtering and washing. The invention provides a simple, efficient, green and environment-friendly novel method for the synthesis of the indole[2,3-b]carbazole compound.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry. technical background [0002] Indolecarbazole and its derivatives have important optical properties and biological activities. Among them, indole[3,2-b]carbazole and its derivatives have attracted extensive attention because of their potential electrical and optical properties. Materials can be prepared as organic light emitting tubes, organic field effect transistors, organic thin film transistors and photovoltaic devices. In addition, indole[2,3-b]carbazole and its derivatives have important biological activities and are important pharmaceutical intermediates, and their derivatives have been widely used in anticancer, antibacterial, antifungal and other research. In view of its importance, various methods for the synthesis of indole[2,3-b]carbazole have been developed. Weike Su et al. reported that indole and benzaldehyde were used as raw materials to synthesize indole[2,3-b]carbaz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00
Inventor 李春张林杨元勇
Owner GUIZHOU MEDICAL UNIV
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