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Polysubstituted carbazole, derivative and synthesis method thereof

A multi-substitution and derivative technology, applied in organic chemistry and other fields, can solve problems such as complex synthesis steps, achieve the effects of saving raw materials, excellent chemical properties, and reducing environmental pollution

Active Publication Date: 2016-11-16
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, and the need to add transition metal catalysts, stoichiometric metal oxidants, etc.

Method used

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  • Polysubstituted carbazole, derivative and synthesis method thereof
  • Polysubstituted carbazole, derivative and synthesis method thereof
  • Polysubstituted carbazole, derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: 9-methyl-2, the synthesis of 4-diphenyl-9-hydrocarbazole

[0054]

[0055] Take a reaction tube, add 0.2mmol (25.0μL) 1-methylindole, 0.2mmol (29.8mg) trans-nitrostyrene, 0.6mmol (70.4μL) acetophenone, 0.04mmol (5.8 mg) ammonium iodide, 0.5 mL of toluene, reacted at 160° C. for 30 hours, and conventionally processed to obtain 56.0 mg of pure product with a yield of 84%.

[0056] The NMR and high-resolution mass spectrometry data of embodiment 1 product are as follows:

[0057] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.76-7.74(m,2H),7.69-7.66(m,2H),7.57(d,J=1.6Hz,1H),7.55-7.44(m,6H),7.41-7.33(m, 4H),7.00-6.96(m,1H),3.87(s,3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ141.8, 141.7, 141.6, 141.2, 138.7, 137.8, 129.2, 128.7, 128.4, 127.5, 127.5, 127.1, 125.5, 122.2, 122.1, 120.2, 119.4, 118.6, 108.2, 105.8 for CHR 25 h 19 N[M+H] + 334.1590,found 334.1592.

Embodiment 2

[0058] Example 2: Synthesis of 7-methyl-5-phenyl-2,3,4,7-tetrahydro-1-hydrobenzo[c]carbazole

[0059]

[0060] Take a reaction tube, add 0.2mmol (25.0μL) 1-methylindole, 0.2mmol (29.8mg) trans-nitrostyrene, 0.6mmol (62.0μL) cyclohexanone, 0.04mmol (5.8 mg) ammonium iodide, 0.5 mL of toluene, reacted at 160° C. for 30 hours, and conventionally processed to obtain 55.4 mg of pure product with a yield of 89%.

[0061] The NMR and high-resolution mass spectrometry data of embodiment 2 product are as follows:

[0062] 1 H NMR (400MHz, CDCl 3 ,ppm)δ8.21(d,J=8.0Hz,1H),7.48-7.34(m,7H),7.23-7.34(m,1H),7.15(s,1H),3.81(s,3H),3.46 (t, J=6.4Hz, 2H), 2.72(t, J=6.2Hz, 2H), 2.05-1.93(m, 2H), 1.84-1.78(m, 2H); 13 C NMR (100MHz, CDCl 3 ,ppm)δ143.1,141.2,140.4,138.9,132.7,129.5,127.9,126.6,125.4,124.7,123.2,123.0,120.1,118.6,108.0,107.4,28.9,28.9,28.6,23.5,23.0 for C cald; 23 h 21 N[M+H] + 312.1747,found 312.1746.

Embodiment 3

[0063] Example 3: Synthesis of 1,9-dimethyl-2,4-phenyl-9-hydrocarbazole

[0064]

[0065] Take a reaction tube, add 0.2mmol (25.0μL) 1-methylindole, 0.2mmol (36.2mg) 1-phenyl-2 nitropropene, 0.6mmol (70.4μL) acetophenone, 0.04 mmol (5.8 mg) of ammonium iodide, 0.5 mL of toluene, reacted at 160° C. for 30 hours, and conventionally processed to obtain 53.5 mg of pure product with a yield of 77%.

[0066] The NMR and high-resolution mass spectrometry data of embodiment 3 product are as follows:

[0067] 1 H NMR (400MHz, CDCl 3 ,ppm)δ7.62-7.60(m,2H),7.51-7.43(m,7H),7.40-7.33(m,4H),7.03(s,1H),6.97-6.93(m,1H),4.18( s,3H),2.77(s,3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ142.8, 142.4, 141.2, 141.1, 140.8, 134.9, 130.0, 129.3, 128.3, 128.0, 127.3, 126.7, 125.4, 123.7, 122.5, 122.2, 120.3, 118.7, 116.9, 108.6 forC 26 h 21 N[M+H] + 348.1747, found 348.1731.

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Abstract

The invention discloses polysubstituted carbazole, a derivative and a synthesis method thereof. The technical scheme includes that under inert gas shielding, three simple components including indole, alkene, and ketone (aldehyde) are adopted for selective synthesis of the polysubstituted carbazole and the derivative for the first time by adoption of ammonium iodide as a catalyst for the first time and adoption of acetonitrile, dichloroethane, tetrahydrofuran, N,N-dimethyl acetyl, benzene, chlorobenzene, orthodichlorobenzene, cyclohexane, 1,4-dioxane, anisole, benzonitrile, dimethylbenzene, trifluorotoluene, methylbenzene, trimethylbenzene and the like as organic solvents. The defect that an existing synthesis method is complex in synthesis steps and requires multi-step synthesis, tradition metal catalysts, chemical equivalent metal oxidizing agents and the like is overcome. The polysubstituted carbazole, the derivative and the synthesis method are widely applicable to various fields of photoelectricity, printing and dyeing, medicines, molecular recognition and the like and is especially suitable for research and development of metal-catalysis-free multi-component one-pot selective synthesis of polysubstituted carbazole compounds.

Description

technical field [0001] The invention relates to a multi-substituted carbazole, derivatives and a synthesis method thereof. Background technique [0002] Carbazole and its derivatives are an important class of nitrogen-containing aromatic heterocyclic compounds, which contain a large conjugated system and strong intramolecular electron transfer. This special rigid fused ring structure makes carbazole compounds exhibit Many unique properties and biological activities have potential wide applications in many fields such as optoelectronic materials, dyes, medicine, and supramolecular recognition. The existing method for synthesizing this type of compound has the disadvantages of complex synthesis steps, multi-step synthesis process is required, and transition metal catalysts and stoichiometric metal oxidants need to be added. Contents of the invention [0003] In view of the above situation, the purpose of this invention is to provide a kind of multi-substituted carbazole and...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/80C07D209/88C07D409/04
CPCC07D209/80C07D209/86C07D209/88C07D409/04
Inventor 邓国军陈善平黄华文
Owner XIANGTAN UNIV
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