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Preparation method of indolocarbazole compound

A technology for indolocarbazoles and compounds, which is applied in the field of preparation of indolocarbazoles, can solve the problems of low diversity of reaction substrates and mild conditions, and achieves wide application range and mild reaction conditions. Effect

Inactive Publication Date: 2019-11-22
ZHEJIANG UNIV
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Problems solved by technology

[0011] The disadvantage of this method is that the diversity of the reaction substrate is not high, the diketone must be a highly symmetrical structure, there is no selectivity, and the reaction must be carried out under reflux under the protection of argon, and the conditions are not mild

Method used

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  • Preparation method of indolocarbazole compound
  • Preparation method of indolocarbazole compound
  • Preparation method of indolocarbazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 6-(4-ethoxyphenyl)-5,12-dimethyl-5,12-dihydroindolo[3,2-a]carbazole

[0050]

[0051] Add 1-ethoxy-4-(2-nitrovinyl)benzene (0.5mmol, 96.5mg), 1-methylindole (1.0mmol, 131mg), trifluoroacetic acid (1.0mmol, 74μL) into 8mL In 1,2-dichloroethane, after the addition, react at room temperature for 24 hours, and spot plate observation. After the reaction was completed, NaOH (1M) was added to the reaction solution to neutralize it to neutrality, and then the column was extracted to obtain a white solid. The extraction is extracted 3 times with ethyl acetate, the combined ethyl acetate layer is washed once with saturated brine, dried over anhydrous sodium sulfate and spin-dried to dry the solvent under reduced pressure, and extracted with silica gel column chromatography, the chromatographic conditions of ethyl acetate : petroleum ether = 1:100.

[0052] White solid, m.p.207.4-208.1℃, 1 H NMR (500MHz, CDCl 3 )δ8.58(d,J=8.0Hz,1H),7.59-7.56(m,2H),7.48-7.46(m,3H),...

Embodiment 2

[0053] Example 2 6-(2-bromophenyl)-5,12-dimethyl-5,12-dihydroindolo[3,2-a]carbazole

[0054]

[0055] The synthesis steps are the same as in Example 1, except that (2-nitrovinyl)benzene is replaced by 1-bromo-2-(2-nitrovinyl)benzene to obtain a white solid.

[0056] White solid, m.p.182.1-182.9℃, 1H NMR (500MHz, CDCl 3 )δ8.61(d, J=8.0Hz,1H),7.83(dd,J=8,1Hz,1H),7.53-7.46(m,5H),7.41-7.37(m,2H),7.31-7.27( m,1H),7.13(s,1H),6.99(t,J=7.5Hz,2H),6.85(d,J=8Hz,1H),4.54(s,3H),3.93(s,3H). 13 C NMR (125MHz, CDCl 3 )δ142.6,141.2,141.1,140.8,137.7,134.7,132.8,131.5,129.3,127.5,124.4,124.2,123.9,123.8,122.8,121.2,120.5,119.5,119.1,114.4,108.9,108.8,106.5,102.9,35.0 , 29.7.HRMS(ESI):m / z calcd for(C 17 h 12 N 2 OS+H) + :439.0804; found: 439.0799.

Embodiment 3

[0057] Example 3 6-(3-bromophenyl)-5,12-dimethyl-5,12-dihydroindolo[3,2-a]carbazole

[0058]

[0059] The synthesis steps are the same as in Example 1, except that (2-nitrovinyl)benzene is replaced by 1-bromo-3-(2-nitrovinyl)benzene to obtain a white solid.

[0060] White solid, m.p.201.1-201.9℃, 1 H NMR (500MHz, CDCl 3 )δ8.60(d, J=8.5Hz, 1H), 7.83(t, J=2Hz, 1H), 7.66-7.64(m, 1H), 7.62-7.60(m, 1H), 7.51-7.48(m, 3H),7.43-7.37(m,2H),7.32-7.27(m,2H),7.12(s,1H),7.05-7.02(m,1H),4.53(s,3H),3.94(s,3H) . 13 C NMR (125MHz, CDCl 3 )δ144.1,141.5,141.1,140.7,138.1,134.7,132.3,131.4,130.6,129.9,128.3,124.4,123.9,123.7,122.8,122.5,121.1,121.0,119.3,119.2,113.8,108.9,106.3,103.3,35.0 , 29.6.HRMS(ESI):m / z calcd for(C 17 h 12 N 2 OS+H) + :439.0804; found: 439.0802.

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Abstract

The invention provides a preparation method of an indolocarbazole compound, and the indolocarbazole compound is prepared through steps of: with substituted indole and nitroolefin as initial raw materials, performing a multi-component reaction under a room-temperature acidic condition. The preparation method provided by the invention has the advantages of mild reaction conditions, simple operation,no need of a metal catalyst, easily available reaction raw materials, simultaneous introduction of a plurality of substituents, easy separation of products and the like, and has a wide substrate application range. According to the method, various substrate structures can tolerate the reaction conditions, the application range is wide, and a simple and feasible method is provided for synthesizingthe indolocarbazole compound. The structural formula of the indolocarbazole compound is shown in the specification.

Description

technical field [0001] The invention belongs to a compound synthesis method and relates to a preparation method of indolocarbazole compounds. Background technique [0002] Indolocarbazole compounds are a class of important molecules, which are mostly used in the preparation of organic electroluminescent materials, organic nonlinear optical materials, photorefractive materials and so on. At present, the synthesis of indolocarbazole compounds includes: [0003] Liang, Li-Na et al. reported that indolo[3,2-a]carbazole was obtained through a multi-step reaction using tryptophan methyl ester and indole as starting materials, (Tetrahedron Lett.2015,56,434-436 .) The specific synthetic route is as follows [0004] [0005] The disadvantage of this method is that the reaction steps are long, and the final decarboxylation reaction temperature is as high as 300 degrees. [0006] Shi, Heping et al. reported that indolo[3,2-a]carbazole was obtained from 1,3-cyclohexanedione and ph...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 陈文腾刘双容应智敏柯迪罗峰俞永平
Owner ZHEJIANG UNIV
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