A kind of synthetic method of benzo [a] carbazole derivative

A technology of carbazole derivatives and synthesis methods, applied in the direction of organic chemistry, etc., can solve the problems of not conforming to the development trend of green chemistry and atomic economics, poor atomic economy, complex synthesis of substrates, etc., and the operation process is simple and feasible. , the steps are simple, the product is easy to purify the effect

Active Publication Date: 2020-04-28
SOUTH CHINA UNIV OF TECH
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  • Description
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Problems solved by technology

Although these reactions obtain products in good yields, there are still many problems: for example, the synthesis of substrates is relatively complex and not universal, and the post-treatment of reactions is cumbersome, which does not conform to green chemistry and atomic economics. development trend
The first is that the reaction does not obtain the target product in one step, and the steps of the reaction are long; secondly, the conditions of this type of reaction are relatively harsh, and it is generally difficult to apply it in actual industrial production; thirdly, the atom economy of this type of reaction is poor

Method used

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  • A kind of synthetic method of benzo [a] carbazole derivative
  • A kind of synthetic method of benzo [a] carbazole derivative
  • A kind of synthetic method of benzo [a] carbazole derivative

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Comparison scheme
Effect test

Embodiment 1

[0045] The synthetic method of benzo [a] carbazole derivative, comprises the following steps:

[0046] (1) In a sealed tube, add 2-phenylindole (19.3mg, 0.1mmol), ethyl acetoacetate diazo (15.6mg, 0.1mmol), anhydrous sodium carbonate (21.2mg, 0.2mmol), anhydrous Sodium acetate water (2.52mg, 0.02mmol), cuprous chloride (5.12mg, 0.05mmol), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (1.5mg, 0.0025mmol) , acetonitrile (2mL), and the mixture was stirred at 80°C for 8h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 20.6 mg of the product with a yield of 68%.

[0047] The structural characterization data of the product obtained in this embodiment are as follows:

[0048] 1 HNMR (400MHz, CDCl 3 )δ9.02(s,1H),8.16(d,J=8.0Hz,1H),8.02–7.94(m,1H),7.93–7.83(m,1H),7.52(d,J=8.1Hz,1H ),7.48–7.37(m,3H),7.28(t,J=7.5Hz,1H),4.59(q,J=7.1Hz,2H),2.90...

Embodiment 2

[0054] The synthetic method of benzo [a] carbazole derivative, comprises the following steps:

[0055] (1) In a sealed tube, add 2-phenylindole (19.3mg, 0.1mmol), ethyl acetoacetate diazo (31.2mg, 0.2mmol), anhydrous sodium carbonate (26.5mg, 0.25mmol), anhydrous Sodium acetate water (2.1mg, 0.025mmol), cuprous chloride (7.42mg, 0.075mmol), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (2.25mg, 0.00375mmol) , acetonitrile (2mL), and the mixture was stirred at 90°C for 8h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 19.6 mg of the product with a yield of 65%.

[0056] The structural characterization data of the product obtained in this embodiment are as follows:

[0057] 1 HNMR (400MHz, CDCl 3 )δ9.02(s,1H),8.16(d,J=8.0Hz,1H),8.02–7.94(m,1H),7.93–7.83(m,1H),7.52(d,J=8.1Hz,1H ),7.48–7.37(m,3H),7.28(t,J=7.5Hz,1H),4.59(q,J=7.1Hz,2H),...

Embodiment 3

[0063] The synthetic method of benzo [a] carbazole derivative, comprises the following steps:

[0064] (1) In a sealed tube, add 2-phenylindole (19.3mg, 0.1mmol), ethyl acetoacetate diazo (31.2mg, 0.2mmol), anhydrous sodium carbonate (21.2mg, 0.2mmol), anhydrous Sodium acetate water (2.52mg, 0.03mmol), cuprous chloride (5.12mg, 0.05mmol), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (3mg, 0.005mmol), Acetonitrile (2 mL), the mixture was stirred at 100°C for 8 h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 21.5 mg of the product with a yield of 71%.

[0065] The structural characterization data of the product obtained in this embodiment are as follows:

[0066] 1 HNMR (400MHz, CDCl 3 )δ9.02(s,1H),8.16(d,J=8.0Hz,1H),8.02–7.94(m,1H),7.93–7.83(m,1H),7.52(d,J=8.1Hz,1H ),7.48–7.37(m,3H),7.28(t,J=7.5Hz,1H),4.59(q,J=7.1Hz,2H),2.90(s,3H...

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Abstract

The invention discloses a method for synthesizing benzo[a]carbazole derivatives. The method comprises dissolving 2-arylindole, a diazo compound, a transition metal salt, an additive, an alkali and a copper salt in an organic solvent, and carrying out a reaction process at 80-100 DEG C in an N2 protective atmosphere for 8-12h to produce benzo[a]carbazole derivatives. The method utilizes the 2-arylindole and diazo compound as raw materials and has mild reaction conditions. The 2-arylindole and diazo compound can be selected from multiple types of compounds. The method is carried out in a strictly anhydrous environment. Reaction processes are more and complex, the reaction occurs at a low temperature and a cooling cost is high. The method is free of water and can construct benzo[a]carbazole derivatives through a one-pot method.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing benzo[a]carbazole derivatives. Background technique [0002] Benzo[a]carbazole is an important skeleton structure of many natural products, drugs, drug intermediates and functional materials. Benzo[a]carbazole and its derivatives have important uses in the field of organic light-emitting semiconductors. At the same time, it can also treat diseases such as tumors, cardiovascular and cerebrovascular diseases, AIDS, obesity, and decreased immunity. In addition, benzo[a]carbazole Azoles are also synthetic precursors for many compounds. Therefore, the synthesis method of benzo[a]carbazole derivatives has been widely paid attention to. [0003] There are two main strategies for the synthesis of benzo[a]carbazole derivatives. One is that transition metals are used as catalysts to catalyze the entire reaction. In 2004, Mamane and Fürstner et al. [Mamane, V.;...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80
CPCC07D209/80
Inventor 曾伟张珍辉
Owner SOUTH CHINA UNIV OF TECH
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