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Method for synthesizing N-substituted carbazole

A synthesis method and carbazole technology are applied in the field of synthesis of high-value chemical fragments-carbazole compounds, which can solve problems such as unfavorable large-scale production, high prices of red phenanthroline and ferrous bromide, influence of drugs and optoelectronic materials, etc. problem, to achieve the effect of green mild reaction conditions

Active Publication Date: 2016-11-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the bathophenanthroline and ferrous bromide used in this method are expensive, which is not conducive to large-scale production
[0010] The above methods all require the participation of transition metals, and even traces of transition metal residues will have adverse effects on drugs and optoelectronic materials

Method used

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  • Method for synthesizing N-substituted carbazole
  • Method for synthesizing N-substituted carbazole
  • Method for synthesizing N-substituted carbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Place (0.224g, 2mmol) potassium tert-butoxide in a dry flask, dissolve (0.309g, 1mmol) 2-iodo-N-methyl-N-phenylaniline and (25mg, 0.4mmol) ethylene glycol In 5mL of dimethyl sulfoxide. The above solution was added dropwise into a dry flask filled with potassium tert-butoxide, and stirred at 30°C for 6 hours. Quench the reaction with saturated sodium chloride, extract three times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, and distill under reduced pressure to remove ethyl acetate. N-methylcarbazole was separated by thin-layer chromatography with a yield of 83.6%.

Embodiment 2

[0033] (0.336g, 3mmol) potassium tert-butoxide was placed in a dry flask, (0.339g, 1mmol) 2-iodo-N-methyl-N-(4-methoxyphenyl)aniline and (15mg, 0.2 mmol) of 1,3-propanediol was dissolved in 5 mL of toluene. The above solution was added dropwise into a dry flask filled with potassium tert-butoxide, and stirred at 50°C for 12 hours. Quench the reaction with saturated sodium chloride, extract three times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, and distill under reduced pressure to remove ethyl acetate. Thin-layer chromatography gave 3-methoxy-9-methylcarbazole with a yield of 76.5%.

Embodiment 3

[0035] (0.560g, 5mmol) potassium tert-butoxide was placed in a dry flask, (0.305g, 1mmol) 2-bromo-N, 4-dimethyl-N-(4-methoxyphenyl) aniline and (44 mg, 0.6 mmol) n-butanol was dissolved in 5 mL of dioxane. The above solution was added dropwise into a dry flask filled with potassium tert-butoxide, and stirred at 100°C for 8 hours. Quench the reaction with saturated sodium chloride, extract three times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, and distill under reduced pressure to remove ethyl acetate. Thin-layer chromatography gave 3-methoxy-6,9-dimethylcarbazole with a yield of 63.8%.

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Abstract

The invention relates to chemical synthesis methods and aims to provide a method for synthesizing N-substituted carbazole. The method comprises the following steps: adding halogenated N-substituted diphenylamine and a ligand into the same solvent for dissolving, dripping the obtained solution into potassium tert-butoxide, and stirring and reacting at the temperature of 30-160 DEG C for 6-12 hours; adding saturated sodium chloride to carry out a quenched reaction, extracting for three times by using ethyl acetate, and merging the organic phase; drying anhydrous sodium sulfate, filtering, performing reduced pressure distillation, removing the ethyl acetate, and performing thin-layer chromatography separation, thereby obtaining the N-substituted carbazole. According to the method disclosed by the invention, the defect in the prior art that transition metals are used is overcome, the reaction conditions are green and mild, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a synthesis method of high-value chemical fragments-carbazole compounds. Background technique [0002] N-substituted carbazoles are an important chemical building block widely found in natural products, medicine and optoelectronic materials. [0003] Yanzhong Li et al. (TETRAHEDRON 2009,65,8961-8968) reported the synthesis method of diiodobiphenyl and primary amine under the catalysis of cuprous iodide and DMEDA to generate N-substituted carbazole, as follows: [0004] [0005] However, this method uses the transition metal copper and the expensive ligand DMEDA, which increases the production cost; and DMEDA is volatile and has a pungent odor, which is not conducive to large-scale production. [0006] [0007] Ying et al. (CHEMICAL COMMUNICATIONS 2014, 50, 9049-9052) reported a synthesis method of 2-aminobiphenyl under the catalysis of palladium carbon, oxygen as an oxidant, ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88
CPCC07D209/86C07D209/88
Inventor 吴军蔺松波顾海宁
Owner ZHEJIANG UNIV
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