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Preparation method of hydroxyl-containing carbazole compound with symmetrical structure

A technology with symmetrical structures and compounds, which is applied in the field of carbazole compound preparation, can solve problems such as the inability to synthesize carbazole compounds quickly and efficiently, expensive and difficult to obtain precious metal catalysts, and limitations of substrate universality, etc., and achieves a fast synthesis rate , easy operation, fast response effect

Inactive Publication Date: 2017-07-25
INNER MONGOLIA UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The traditional carbazole synthesis method has harsh reaction conditions, complicated steps, and difficulty in separation and purification
In recent years, many transition metal-catalyzed cascade reactions have been applied to the synthesis of carbazole compounds, but these methods require the use of expensive and difficult-to-obtain noble metal catalysts, and the universality of substrates is also limited.
Moreover, all these methods cannot rapidly and efficiently synthesize structurally symmetrical hydroxyl-containing carbazole compounds

Method used

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  • Preparation method of hydroxyl-containing carbazole compound with symmetrical structure
  • Preparation method of hydroxyl-containing carbazole compound with symmetrical structure
  • Preparation method of hydroxyl-containing carbazole compound with symmetrical structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 1, 4, 5, 8-tetraphenyl-3, 6-dihydroxy-9H-carbazole

[0026] Add 34 mg (ie 0.5 mmol) of pyrrole, 354 mg (ie 1.5 mmol) of 1,4-diphenyl-3-butene-1,2-dione, 36 mg (ie 0.1 mmol) into a 25 mL glass reaction vial ) Trifluoromethanesulfonic acid ketone, then add 4 mL 1,4-dioxane, at 25 o C under stirring for 2 hours, adding 10 mg (i.e. 0.05 mmol) p-toluenesulfonic acid monohydrate, at 70 o Stir at C for 3 hours, concentrate after reaction, use petroleum ether: ethyl acetate volume ratio of 10:1 as eluent, and purify by silica gel column chromatography to obtain 1, 4, 5, 8-tetraphenyl-3 , 6-dihydroxy-9H-carbazole, its structure is shown in the following formula:

[0027]

[0028] This compound is yellow solid, and productive rate is 52%, and its nuclear magnetic data is as follows:

[0029] 1 H NMR (500 MHz, CDCl 3 ) δ 4.75 (s, 1H), 6.85 - 6.70 (dd, J 1 = 7.0 Hz, J 2 =1.5 Hz, 4H), 7.03 - 7.11 (s, 6 H), 7.13 (s, 2H), 7.40 - 7.43 (t, J = 7.5 Hz,2H), 7....

Embodiment 2

[0031] Synthesis of 1, 8-bis(4-fluorophenyl)-4, 5-diphenyl-9H-carbazole

[0032] Add 34 mg (ie 0.5 mmol) of pyrrole and 381 mg (ie 1.5 mmol) of 1-(4-fluorophenyl)-4-phenyl-3-butene-1,2-dione into a 25mL glass reaction vial , 36 mg (ie 0.1 mmol) trifluoromethanesulfonic acid ketone, then add 4mL 1,4-dioxane, at 25 o C under stirring for 1 hour, adding 10 mg (ie 0.05 mmol) p-toluenesulfonic acid monohydrate, at 70 o Stirring at C for 3 hours, concentrated after reaction, using petroleum ether:ethyl acetate volume ratio of 10:1 as eluent, purified by silica gel column chromatography to obtain 1,8-bis(4-fluorophenyl)- 4, 5-diphenyl-9H-carbazole, its structure is shown in the following formula:

[0033]

[0034] This compound is yellow solid, and productive rate is 46%, and its NMR data is as follows:

[0035] 1 H NMR (500 MHz, CDCl 3 ) δ 4.77 (s, 2H), 6.82 - 6.84 (dd, J 1 = 7.5Hz, J 2 =1.5 Hz, 4H), 7.17 - 7.12 (m, 8 H), 7.50 - 7.52 (d, J = 8.5 Hz, 4H), 7.61 -7.63 (...

Embodiment 3

[0037] Synthesis of 1, 8-bis(2-chlorophenyl)-4, 5-diphenyl-9H-carbazole

[0038] Add 34 mg (ie 0.5 mmol) of pyrrole and 407 mg (ie 1.5 mmol) of 1-(2-chlorophenyl)-4-phenyl-3-butene-1, 2-dione into a 25 mL glass reaction vial , 36 mg (ie 0.1 mmol) trifluoromethanesulfonic acid ketone, then add 5mL 1,4-dioxane, at 25 o C under stirring for 1 hour, adding 10 mg (ie 0.05 mmol) p-toluenesulfonic acid monohydrate, at 70 o Stirring at C for 4 hours, concentrated after reaction, using petroleum ether: ethyl acetate volume ratio of 10:1 as eluent, purified by silica gel column chromatography to obtain 1, 8-bis(2-chlorophenyl)- 4, 5-diphenyl-9H-carbazole, its structure is shown in the following formula:

[0039]

[0040]This compound is yellow solid, and productive rate is 37%, and its NMR data is as follows:

[0041] 1 H NMR (500 MHz, CDCl 3 ) δ 4.75 (s, 2H), 6.85 - 6.87 (dd, J 1 = 7.5Hz, J 2 =1.5 Hz,, 4H), 7.07 - 7.10 (m, 6H), 7.13 (s, 2H) 7.23 - 7.30 (m, 4H), 7.38 -7.41...

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Abstract

The invention discloses a preparation method of a hydroxyl-containing carbazole compound with a symmetrical structure. The preparation method comprises the following steps: reacting pyrrole with a 3-ene-1,2-dione compound in an organic solvent under the catalysis of copper trifluoromethane sulfonate, to obtain a 3,6-dihydroxyl carbazole compound. According to the invention, the reaction occurs in the air without requiring a strict anhydrous oxygen-free condition, the operation is simple and convenient, the reaction speed is high, the product specificity is good, few side products are generated, and the tolerance to functional groups is good. The invention provides a simple and convenient high-efficiency preparation method of 3,6-dihydroxyl-containing carbazole compound with symmetrical structure for the first time.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing a symmetrically structured hydroxyl-containing carbazole compound. Background technique [0002] Carbazole and its derivatives are an important class of heterocyclic compounds, which are widely used in scientific research and industrial production. Studies have found that many natural products, bioactive molecules and pesticides contain carbazole structural units. In addition, carbazole derivatives also have important applications in dyes, photoelectric functional materials and supramolecular recognition. Therefore, the synthesis of new carbazole compounds is of great significance to the development of new biologically active molecules, the development of new drugs and the synthesis of new materials. The traditional synthesis method of carbazole has harsh reaction conditions, cumbersome steps, and difficulty in separation and purification. In recent year...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 陈树峰乔羽吴新星龙振兴
Owner INNER MONGOLIA UNIVERSITY
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