Synthetic method for aromatic[a]carbazole compounds

A synthetic method and compound technology, applied in organic chemistry and other fields, can solve the problems of difficult to obtain raw materials, harsh reaction conditions, and low atom economy, and achieve the effects of wide application range, mild reaction conditions, and high atom economy

Active Publication Date: 2017-04-26
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In view of its importance, people have successively developed some effective methods for constructing the structure of benzocarbazole, but these methods still have problems such as difficult access to raw materials, harsh reaction conditions, cumbersome operation steps, and low atom economy, which make them The application in actual production is very limited

Method used

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  • Synthetic method for aromatic[a]carbazole compounds
  • Synthetic method for aromatic[a]carbazole compounds
  • Synthetic method for aromatic[a]carbazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] Add compound 1a (0.5mmol, 96.6mg), compound 2a (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg), copper acetate (0.05mmol, 9.1mg) into the 15mL reaction tube. mg) and acetonitrile (3mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 18h. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine successively, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 5-ethoxyacyl-6-phenyl-11H-benzo[a]carbazole 3a (129.7mg, 71%). The characterization data of this compound are as follows: 1 H NMR(600MHz, CDCl 3 )δ:0.96(t,J=7.2Hz,3H), 4.12(q,J=7.2Hz,2H), 6.90(d,J=8.4Hz,1H), 6.99(t,J=7.8Hz,1H) ,7.35(t,J=7.8Hz,1H),7.51-7.55(m,6H),7.57-7.61(m,2H),8.14-8.15(m,1H),8.17-8.18...

Embodiment 2

[0022] According to the method described in Example 1, add compound 1a (0.5mmol, 96.6mg), compound 2a (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg) into a 15mL reaction tube ), silver acetate (0.5mmol, 83.5mg) and 1,2-dichloroethane (3mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 18h. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine successively, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 5-ethoxyacyl-6-phenyl-11H-benzo[a]carbazole 3a (60.3mg, 33%).

Embodiment 3

[0024] According to the method described in Example 1, add compound 1a (0.5mmol, 96.6mg), compound 2a (0.75mmol, 163.7mg), dicyclopentadienyl rhodium dichloride (0.025mmol, 15.5mg) into a 15mL reaction tube ), silver acetate (0.5mmol, 83.5mg) and methanol (3mL), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 18h. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine successively, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 5-ethoxyacyl-6-phenyl-11H-benzo[a]carbazole 3a (27.4mg, 15%).

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Abstract

The invention discloses a synthetic method for aromatic[a]carbazole compounds, belonging to the technical field of organic synthesis. According to a technical scheme in the invention, the synthetic method comprises the following steps: dissolving a 2-phenylindole compound, 2-(naphth-1-yl)indole compound or 2-(thiazol-1-yl)indole compound and a diazo compound in a solvent together; then adding a catalyst and an additive; and carrying out a reaction at 100 to 140 DEG C so as to prepare a benzo[a]carbazole compound, naphtho[a]carbazole compound or thiazolo[a]carbazole compound. According to the invention, 2-substituted indole compounds and the diazo compound are used as raw materials and subjected to a one-pot cascade reaction so as to directly obtain the aromatic[a]carbazole compounds; and the synthetic method is simple and convenient in process, mild in conditions, wide in a substrate adaptability range and suitable for industrial production.

Description

Technical field [0001] The present invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing aromatic cyclo[a]carbazole compounds. Background technique [0002] Benzocarbazole and its derivatives have important biological activity and optical properties, and are common structural units in many fine chemicals (such as pesticides, pesticides, medicine, rubber, nonlinear optical materials, etc.). In addition, by introducing different functional groups on the benzocarbazole skeleton, its biological activity, fluorescence efficiency, and laser quantum efficiency can also be adjusted, so as to achieve the purpose of improving its application value. In view of its importance, people have successively developed some effective methods for constructing the benzocarbazole structural framework. However, these methods still have problems such as difficult access to raw materials, harsh reaction conditions, cumbersome operation steps, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D409/04C07D495/04
CPCC07D209/80C07D409/04C07D495/04
Inventor 范学森李彬张新迎张蓓蓓何艳
Owner HENAN NORMAL UNIV
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