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Synthesis method of 11H-indolo [3,2-c] quinoline compounds

A synthesis method and technology of aldehyde compounds, applied in the field of synthesis of 11H-indolo[3,2-c]quinoline compounds, capable of solving problems such as limited application range, narrow substrate application range, and harsh reaction conditions , to achieve the effect of high regioselectivity, wide range of substrate application and simple operation

Inactive Publication Date: 2015-12-30
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These literature methods have disadvantages such as difficulty in obtaining starting materials, use of expensive catalysts, narrow scope of substrate application, harsh reaction conditions, and low yields, which largely limit the scope of application of this type of synthetic method.

Method used

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  • Synthesis method of 11H-indolo [3,2-c] quinoline compounds
  • Synthesis method of 11H-indolo [3,2-c] quinoline compounds
  • Synthesis method of 11H-indolo [3,2-c] quinoline compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] In a 15mL sealed tube, add 1a (0.4mmol, 109mg), dimethylsulfoxide (1.5mL), potassium carbonate (0.8mmol, 111mg), cuprous iodide (0.04mmol, 7.6mg), L-proline (0.08mmol, 9.2mg) , 2a (0.8mmol, 86mg) and 26% concentrated ammonia water (0.4mL, 2.8mmol), then the mixture was sealed and heated to 100°C, and reacted under nitrogen for 12h. Next, add hydrochloric acid (6M, ca. 0.7mL) to adjust the reaction system to weak acidity (pH=5-6), and then heated at 120°C for 8h. After the reaction was completed, saturated sodium bicarbonate was added to the sealed tube to quench the reaction, extracted with chloroform, and then the organic phase was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain white solid 6-phenyl-11 H -Indolo[3,2- c ]quinoline 3a (95mg, 81%). The characterization data of this compound are as foll...

Embodiment 2

[0017] According to the method described in Example 1, in a 15mL sealed tube, add 1a (0.4mmol, 109mg), dimethylsulfoxide (1.5mL), potassium carbonate (0.8mmol, 111mg), cuprous iodide (0.04mmol, 7.6mg), L-proline (0.08mmol, 9.2mg) , 2a (0.8mmol, 86mg) and 26% concentrated ammonia water (0.4mL, 2.8mmol), then the mixture was sealed and heated to 100°C, and reacted under nitrogen for 12h. Next, add hydrochloric acid (6M, ca. 0.7mL) to adjust the reaction system to weak acidity (pH=5-6), and then heated at 100°C for 8h to obtain the product 6-phenyl-11 H -Indolo[3,2- c ]quinoline 3a (82mg, 70%).

Embodiment 3

[0019] According to the method described in Example 1, in a 15mL sealed tube, add 1a (0.4mmol, 109mg), dimethyl sulfoxide (1.5mL), potassium carbonate (0.8mmol, 111mg), cuprous chloride (0.04mmol, 4.0mg), L-proline (0.08mmol, 9.2mg) , 2a (0.8mmol, 86mg) and 26% concentrated ammonia water (0.4mL, 2.8mmol), then the mixture was sealed and heated to 100°C, and reacted under nitrogen for 12h. Next, add hydrochloric acid (6M, ca. 0.7mL) to adjust the reaction system to weak acidity (pH=5-6), and then heated at 100°C for 8h to obtain the product 6-phenyl-11 H -Indolo[3,2- c ]quinoline 3a (65 mg, 55%).

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Abstract

The invention discloses a synthesis method of 11H-indolo [3,2-c] quinoline compounds, belonging to the technical field of synthesis of indolo quinoline compounds. The technical scheme of the invention is mainly characterized by taking 2-(2-bromo-aryl)-1H-indolo, ammonia water and aldehyde compounds as raw materials, taking dimethyl sulfoxide or N,N-dimethyl formamide as a solvent, taking transition metal salt as a catalyst, taking potassium carbonate as alkali, and taking L-proline as a ligand to carry out one-pot, two-step and three-component tandem reaction to synthesize 11H-indolo [3,2-c] quinoline compounds with multiple substitute modes. The synthesis method disclosed by the invention has the advantages that starting materials are simple and easy to prepare, and substrates are wide in range of application, high in regioselectivity and simple in operation.

Description

technical field [0001] The invention belongs to the technical field of synthesis of indoloquinoline compounds, in particular to a 11 H -Indolo[3,2- c ] The synthetic method of quinoline compound. Background technique [0002] Indoloquinoline compounds widely exist in natural products and synthetic drugs with broad-spectrum biological activities, and have attracted extensive attention of chemists in recent years. Among them, 11 H -Indolo[3,2- c ]Quinoline compounds can not only be used as anti-malarial and anti-cancer drug candidates, high-efficiency inhibitors of protein kinase DYRK1A, but also can be used as DNA intercalators to inhibit DNA replication and transcription, and have important roles in the fields of biology and medicine. application value. 11 reported in related literature H -Indolo[3,2- c ] The synthetic methods of quinolines are mainly prepared by palladium-catalyzed insertion reaction of isocyanide, gold-catalyzed cyclization reaction of acyclic alkyn...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 郭胜海陶丽范学森张新迎
Owner HENAN NORMAL UNIV
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