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Areno [c] carbazoles derivative and synthetic method thereof

A synthetic method and derivative technology, applied in the direction of organic chemistry, can solve problems such as complex synthetic steps, and achieve the effect of simple reaction system, high product utilization value, and stable molecular structure

Active Publication Date: 2018-01-23
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Areno [c] carbazoles derivative and synthetic method thereof
  • Areno [c] carbazoles derivative and synthetic method thereof
  • Areno [c] carbazoles derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0064]

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

[0066] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0067] 1H NMR (400MHz, CDCl3) δ8.83(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), 4.50(t , J=6.8Hz, 2H), 3.99(s, 3H), 1.90-1.83(m, 2H), 1.60-1.50(m, 2H), 1.03(t, J=7.4Hz, 3H); 13...

Embodiment 2、3

[0079] Embodiment 2,3 3, the synthesis of 7-dimethyl-7H-benzo [c] carbazole-6-butyl carboxylate

[0080]

[0081] 1H NMR (400MHz, CDCl3) δ8.72(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) δ168.1, 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, Synthesis of 7-methyl-3-ethyl-7H-benzo[c]carbazole-6-butyl carboxylate

[0083]

[0084] 1H NMR (400MHz, CDCl3) δ8.74(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) δ168. for C24H26NO2[M+H]+360.1958, found 360.1957.

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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 fields of organic light-emitting semiconductors, drugs, and materials. In addition, arylcarbazole is also a precursor for the synthesis of many compounds. Therefore, the synthetic method of aromatic ring carbazole derivatives has been widely paid attention to. The existing methods for synthesizing such compounds have the disadvantages of complex synthesis steps, which require multi-step synthesis processes, the addition of transition metal catalysts, stoichiometric metal oxidants, and the use of relatively high-activity starting materials. Contents of the invention [0003] In view of the above situation, the obje...

Claims

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Application Information

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Patent Type & Authority Applications(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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