Method for preparing N-heterocyclic aromatic hydrocarbon derivatives by dehalogenation and alkylation

A technology for heterocyclic aromatic hydrocarbons and alkylation, which is applied in the field of preparing N-heterocyclic aromatic hydrocarbon derivatives, can solve the problems of difficulty in achieving high regioselectivity, few synthesis methods, etc., and achieves wide application range of substrates and cheap reagents. , mild conditions

Active Publication Date: 2019-05-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the products obtained by existing CDC reactions are often multi-site substitution products, and it is difficult to achieve high regioselectivity.
Through the selective dehalogenation and alkylation of halogenated N-heterocyclic aromatic hydrocarbons, "site-directed substitution products" can be obtained, but there are few synthetic methods in this area, which has great research value

Method used

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  • Method for preparing N-heterocyclic aromatic hydrocarbon derivatives by dehalogenation and alkylation
  • Method for preparing N-heterocyclic aromatic hydrocarbon derivatives by dehalogenation and alkylation
  • Method for preparing N-heterocyclic aromatic hydrocarbon derivatives by dehalogenation and alkylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 4,7-dichloroquinoline (0.5mmol, 99mg), tetrahydrofuran (10mmol, 720mg), CuBr (0.025mmol, 3.6mg), selective fluorine reagent (1mmol, 354.3mg) and trifluoromethanesulfonic acid (0.5mmol , 75 mg) was added to a 5 mL single-port reaction flask, acetonitrile (5.0 mL) was added as a solvent, and the oil bath was heated to 50° C. for 5 h. After the reaction, the reaction solution was washed with water and extracted with ethyl acetate, and then separated into an organic layer and an aqueous layer. The organic layer was dried over anhydrous sodium sulfate and concentrated by distillation under reduced pressure to obtain a yellow oil. The yellow oil was separated by column chromatography, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1 as the eluent, the eluate containing the target compound was collected, the solvent was evaporated and dried to obtain 87.5 mg of light yellow oil 7 -Chloro-4-(tetrahydrofuran-2-yl)quinoline, the yield is 75%, and i...

Embodiment 2

[0034] The protonic acid in the system was replaced with trifluoroacetic acid (0.5mmol, 57mg), and other operating conditions were the same as in Example 1, and finally 70.3mg of light yellow oily substance 7-chloro-4-(tetrahydrofuran-2-yl)quinoline was obtained. Yield 60%.

Embodiment 3

[0036] The THF dosage was changed to 2.5 mmol, and the other operating conditions were the same as in Example 1 to finally obtain 60.6 mg of light yellow oil 7-chloro-4-(tetrahydrofuran-2-yl)quinoline with a yield of 52%.

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Abstract

The invention discloses a method for preparing N-heterocyclic aromatic hydrocarbon derivatives by dehalogenation and alkylation. The method includes: dissolving halogenated N-heterocyclic aromatic hydrocarbon compounds, ether compounds, copper salts, an N-F reagent and protonic acid into an organic solvent, stirring in oil bath, performing reaction for 3-20h at a temperature of 20-60 DEG C, and after reaction is finished, treating reaction liquid to obtain the N-heterocyclic aromatic hydrocarbon derivatives. The method has advantages that dehalogenation and alkylation of the N-heterocyclic aromatic hydrocarbon compounds are realized under catalysis of the copper salts, high regioselectivity in reaction is achieved, a reaction substrate application range is expanded, and selective dehalogenation and alkylation of halogenated heterocyclic aromatic hydrocarbon compounds such as halogenated quinoline derivatives, halogenated isoquinoline derivatives, halogenated benzoxazole derivatives andhalogenated benzothiazole derivatives can be realized.

Description

technical field [0001] The invention relates to a method for preparing N-heterocyclic aromatic hydrocarbon derivatives through dehalogenation and alkylation. Background technique [0002] N-heterocyclic aromatic hydrocarbon derivatives are an important class of natural compounds, which widely exist in the plant kingdom. Studies have shown that N-heterocyclic aromatic hydrocarbon derivatives have good biological activity, have remarkable effects in antibacterial, anti-inflammatory, anti-cancer, and anti-HIV viruses, and are widely used in the field of medicine. In recent years, the synthesis of alkyl-substituted N-heterocyclic aromatic compounds has received extensive attention, and some progress has been made, but the dehalogenation and alkylation reactions of halogen-containing N-heterocyclic aromatic compounds are rarely reported. great research value. [0003] Before the present invention, mainly prepare N-heterocyclic aromatic hydrocarbon derivatives by the cross dehyd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D215/14C07D417/04C07D413/04
Inventor 周嘉第李坚军邹亚文周鹏
Owner ZHEJIANG UNIV OF TECH
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