A kind of aromatic ring [c] carbazole derivatives and its synthesis method

A synthetic method and derivative technology, applied in the direction of organic chemistry, etc., can solve problems such as complex synthetic steps, and achieve the effect of simple reaction system, excellent chemical properties, and cheap and easy-to-obtain raw materials

Active Publication Date: 2020-10-13
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing methods for synthesizing such compounds have complex synthesis steps, which require multi-step synthesis processes to complete, need to add transition metal catalysts, stoichiometric metal oxidants, and use relatively high-activity starting materials, etc.

Method used

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  • A kind of aromatic ring [c] carbazole derivatives and its synthesis method
  • A kind of aromatic ring [c] carbazole derivatives and its synthesis method
  • A kind of aromatic ring [c] carbazole derivatives and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1 Synthesis of 7-methyl-7H-benzo[c]carbazole-6-carboxylic acid butyl ester

[0064]

[0065] Take a reaction tube, add 0.02mmol (2.9mg) amine iodide, 0.2mmol (25.0μL) 1-methyl indole, 0.4mmol (41.6μL) cyclohexanone, 0.4mmol (57.6μL) butyl acrylate, 0.5 mL of toluene was stirred at 150 °C to carry out the first step of the reaction for 24 hours. After cooling, 0.9 mmol (204.3 mg) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and 0.1 mL of toluene were added. Carry out the second step reaction, the reaction temperature is 50° C., the reaction is stirred for 24 hours, and 50.3 mg of pure product is obtained by conventional treatment, and the yield is 76%.

[0066] The nuclear magnetic and mass spectrometry data of the product of Example 1 are as follows:

[0067] 1H NMR (400MHz, CDCl3) δ 8.83 (d, J=8.4Hz, 1H), 8.61 (d, J=8.0Hz, 1H), 8.29 (s, 1H), 8.04 (d, J=8.0Hz, 1H) ), 7.77(t, J=7.8Hz, 1H), 7.61(d, J=8.4Hz, 1H), 7.57-7.48(m, 2H), 7.42(t, J=7.4Hz, 1H), 4.5...

Embodiment 2、3

[0079] Example 2, 3 Synthesis of 3,7-dimethyl-7H-benzo[c]carbazole-6-carboxylic acid butyl ester

[0080]

[0081] 1H NMR (400MHz, CDCl3) δ 8.72(d, J=8.4Hz, 1H), 8.58(d, J=8.0Hz, 1H), 8.22(s, 1H), 7.81(s, 1H), 7.61-7.58 (m, 2H), 7.53 (t, J=8.0Hz, 1H), 7.40 (t, J=7.4Hz, 1H), 4.49 (t, J=6.8Hz, 2H), 3.97 (s, 3H), 2.57 (s, 3H), 1.89-1.82 (m, 2H), 1.59-1.50 (m, 2H), 1.03 (t, J=7.4Hz, 3H); 13C NMR (100MHz, CDCl3) δ 168.1, 141.4, 135.2 ,132.9,130.8,129.6,129.3,129.0,127.8,124.7,123.0,122.9,122.0,120.1,117.9,117.3,109.7,65.4,33.3,30.8,21.4,19.3,13.8; ]+346.1802, found 346.1804.

Embodiment 4、5

[0082] Example 4, 5 Synthesis of 7-methyl-3-ethyl-7H-benzo[c]carbazole-6-carboxylic acid butyl ester

[0083]

[0084] 1H NMR (400MHz, CDCl3) δ 8.74(d, J=8.8Hz, 1H), 8.58(d, J=8.0Hz, 1H), 8.24(s, 1H), 7.82(s, 1H), 7.64-7.51 (m, 3H), 7.39 (t, J=7.6Hz, 1H), 4.48 (t, J=6.8Hz, 2H), 3.97 (s, 3H), 2.87 (q, J=7.6Hz, 2H), 1.89 -1.82 (m, 2H), 1.58-1.50 (m, 2H), 1.37 (t, J=7.6Hz, 3H), 1.03 (t, J=7.4Hz, 3H); 13C NMR (100MHz, CDCl3) δ 168. HRMS calcd.8; HRMS calcd.8 C24H26NO2[M+H]+360.1958, found360.1957.

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Abstract

The invention relates to an areno [c] carbazoles derivative and a synthetic method thereof. According to the technical scheme, environmentally friendly and low-price ammonium iodide is used as a catalyst, 2,3-dichloro-5,6-dicyano benzoquinone as an oxidizing agent, a mixture of one or more of hexamethylene, toluene, dimethylbenzene, trimethylbenzene, benzotrifluoride, ethylbenzene, chlorobenzene,o-dichlorohenzene, anisole, decahydronaphthalene and 1,4-dioxane is used as an organic solvent, and simple raw materials including an indoles derivative, a cyclohexanones derivative and olefins derivative are synthesized into areno [c] carbazole and a derivative thereof in a pot. The shortcomings that by an existing synthetic method, when a metal catalyst or a metal oxidizing agent requires or a starting raw material with relatively high activity requires, synthesis steps are complicated, reaction conditions are severe and the like are overcome. The synthetic method is suitable for preparing the areno [c] carbazoles derivative with certain photoelectric property, bioactivity and drug activity.

Description

technical field [0001] The invention relates to an aromatic ring [c]carbazole derivative and a synthesis method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Aromatic carbazole is an important skeleton structure of many natural products, drugs, drug intermediates, and functional materials, and is widely used in the field of organic light-emitting semiconductors, drugs and materials. In addition, the aromatic ring carbazole is also a precursor for the synthesis of many compounds. Therefore, the synthesis methods of aromatic carbazole derivatives have been widely paid attention to. The existing methods for synthesizing such compounds have the disadvantages of complex synthesis steps, requiring multi-step synthesis processes, adding transition metal catalysts, stoichiometric metal oxidants, and using relatively active starting materials. SUMMARY OF THE INVENTION [0003] In view of the above situation, the purpose of the prese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80
Inventor 邓国军陈善平黄华文肖福红
Owner XIANGTAN UNIV
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