Synthetic method of 5-acylbenzo[a]carbazole compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions, low atom economy, and complicated operation steps, and achieve the effects of easy availability of raw materials, simple synthesis process, and high synthesis efficiency.

Active Publication Date: 2018-09-04
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although most of the synthesis strategies in these literatures are relatively effective and reliable, there are still some problems to be solved, such as difficult to obtain raw materials, harsh reaction conditions, cumbersome operation steps, low atom economy, etc., which make their application in actual production restricted

Method used

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  • Synthetic method of 5-acylbenzo[a]carbazole compound
  • Synthetic method of 5-acylbenzo[a]carbazole compound
  • Synthetic method of 5-acylbenzo[a]carbazole compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011]

[0012] Add 1a (0.5mmol, 110.6mg), tetrahydrofuran (3mL), 2a (0.75mmol, 147.2mg), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer in the 15mL reaction tube in sequence ([RhCp*Cl 2 ] 2 , 0.025mmol, 15.4mg) and cesium acetate (0.25mmol, 48.0mg), the reaction tube was sealed under air conditions, and then placed in an oil bath at 100°C and stirred for 12h. After the reaction, the reaction tube was cooled to room temperature, 10 mL of water was added, and then extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in turn, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain a yellow solid product 3a (136.2 mg, 85%). The characterization data of this compound are as follows: 1 H NMR(600MHz, DMSO-d 6 ): δ 7.23(t,J=7.2Hz,1H), 7.46(t,J=6.6Hz,1H), 7.56(t,J=6.6Hz,2H), 7.61(t,J=7.2Hz,1H) ,7.68(t,J=6.6Hz,1H), 7.73(d,J=...

Embodiment 2

[0014] Add 1a (0.5mmol, 110.6mg), 1,2-dichloroethane (3mL), 2a (0.75mmol, 147.2mg), (RhCp*Cl 2 ] 2 (0.025mmol, 15.4mg) and cesium acetate (0.25mmol, 48.0mg), the reaction tube was sealed under air conditions, and then placed in an oil bath at 100°C and stirred for 12h. After the reaction, the reaction tube was cooled to room temperature, 10 mL of water was added, and then extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in turn, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain a yellow solid product 3a (57.8 mg, 36%).

Embodiment 3

[0016] Add 1a (0.5mmol, 110.6mg), methylene chloride (3mL), 2a (0.75mmol, 147.2mg), (RhCp*Cl 2 ] 2 (0.025mmol, 15.4mg) and cesium acetate (0.25mmol, 48.0mg), the reaction tube was sealed under air conditions, and then placed in an oil bath at 100°C and stirred for 12h. After the reaction, the reaction tube was cooled to room temperature, 10 mL of water was added, and then extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in turn, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain a yellow solid product 3a (54.6 mg, 34%).

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Abstract

The invention discloses a synthetic method of a 5-acylbenzo[a]carbazole compound. According to the synthetic method, the 5-acylbenzo[a]carbazole compound is synthesized through cascade reaction between a 2-aryl-3-formylhydrazine compound and sulfur ylide. The synthetic method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like and is suitable for industrial production.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing 5-acylbenzo[a]carbazole compounds. Background technique [0002] As an important type of nitrogen-containing fused heterocyclic ring, benzo[a]carbazole is commonly found in natural product molecules and is the basic structural unit of many compounds with significant biological and pharmaceutical activity. Recent research results show that benzo[a]carbazole can also be used as the core framework for many organic light-emitting devices to realize the functions of light emission, hole transport, and host materials, and has important application value in the development of organic functional materials. It should be pointed out that the introduction of acyl groups at the 5-position of benzo[a]carbazole can not only regulate the biological activity and luminescence properties of the corresponding benzo[a]carbazole derivatives, but also make use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D409/06
CPCC07D209/80C07D409/06
Inventor 张新迎陈光李彬贾瑞雪
Owner HENAN NORMAL UNIV
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