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Bromination reaction method of nitrogen-containing heterocyclic compound and application

A nitrogen heterocyclic compound, bromination reaction technology, applied in the direction of organic chemistry, can solve the problem of debromination products, etc., to achieve the effect of good yield, high selectivity, and good atom economy

Pending Publication Date: 2021-11-30
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the regional control of the existing preparation methods mainly depends on the substrate, and has side reactions such as debrominated products and overbrominated

Method used

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  • Bromination reaction method of nitrogen-containing heterocyclic compound and application
  • Bromination reaction method of nitrogen-containing heterocyclic compound and application
  • Bromination reaction method of nitrogen-containing heterocyclic compound and application

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Experimental program
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Embodiment 1

[0049] This embodiment provides a method for the bromination reaction of nitrogen-containing heterocyclic compounds, the reaction formula of which is:

[0050]

[0051] The specific operation steps are:

[0052] In air, add magneton, N-benzyl-5-nitroquinoline quaternary ammonium salt I-a (0.1mmol, 29.9mg), N-bromosuccinimide (0.2mmol , 34.8mL), benzoic acid (0.05mmol, 6.1mg), dichloroethane (1.5mL). Then put on a rubber stopper and heat and stir in an oil bath at 100°C for 4h. After the reaction was completed, the reaction system was cooled to room temperature, filtered with a glass sand funnel lined with diatomaceous earth, washed with dichloromethane and ethyl acetate, combined the filtrates, evaporated the solvent under reduced pressure, added 10 mL of distilled water, and then used 30 mL The ethyl acetate is divided into 3 extractions, and the extract is dried with anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure, and petroleum ether / eth...

Embodiment 2

[0056] This embodiment provides a method for the bromination reaction of nitrogen-containing heterocyclic compounds, the reaction formula of which is:

[0057]

[0058] The specific operation steps are:

[0059] In air, to a 25 mL reaction tube was added magneton, N-benzyl-2-(naphthyl-1-yl)pyridinium quaternary ammonium salt I-c (0.1 mmol, 37.5 mg), N-bromosuccinyl Imine (0.2mmol, 34.8mL), p-fluorobenzoic acid (0.05mmol, 6.1mg), dichloroethane (1.5mL). Then put on a rubber stopper and heat and stir in an oil bath at 100°C for 4h. After the reaction was completed, the reaction system was cooled to room temperature, filtered with a glass sand funnel lined with diatomaceous earth, washed with dichloromethane and ethyl acetate, combined the filtrates, evaporated the solvent under reduced pressure, added 10 mL of distilled water, and then used 30 mL The ethyl acetate was extracted three times, the extract was dried with anhydrous magnesium sulfate, the solvent was evaporated u...

Embodiment 3

[0066] This embodiment provides a method for the bromination reaction of nitrogen-containing heterocyclic compounds, the reaction formula of which is:

[0067]

[0068] The specific operation steps are:

[0069] In air, add magneton, N-benzyl-2-phenylpyridinium quaternary ammonium salt I-d (0.1mmol, 32.5mg), N-bromosuccinimide (0.2mmol, 34.8mL), 2-fluorobenzoic acid (0.05mmol, 7.0mg), dichloroethane (1.5mL). Then put on a rubber stopper and heat and stir in an oil bath at 100°C for 16h. After the reaction was completed, the reaction system was cooled to room temperature, filtered with a glass sand funnel lined with diatomaceous earth, washed with dichloromethane and ethyl acetate, combined the filtrates, evaporated the solvent under reduced pressure, added 10 mL of distilled water, and then used 30 mL The ethyl acetate was extracted three times, the extract was dried with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, petroleum ether / ethyl...

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Abstract

The invention discloses a bromination reaction method of a nitrogen-containing heterocyclic compound and application, and relates to the technical field of organic synthesis. The bromination reaction method of a nitrogen-containing heterocyclic compound comprises the following step of: reacting C-H activated nitrogen-containing heterocyclic benzyl quaternary ammonium salt with a bromination reagent in the presence of an additive, wherein the additive is at least one of organic acid and organic alkali, and the nitrogen-containing heterocyclic benzyl quaternary ammonium salt is at least one of N-benzyl quinoline quaternary ammonium salt and N-benzyl-2-phenylpyridine quaternary ammonium salt. The method has the advantages of good yield, high selectivity and better atom economy, and is suitable for popularization and application. The bromination product, namely, a dibromoquinoline compound or a dibromopyridine compound, is further subjected to a coupling reaction to obtain complex compound molecules and drug molecules with a greater application potential.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method and application of bromination reaction of nitrogen-containing heterocyclic compounds. Background technique [0002] Brominated nitrogen-containing heterocyclic compounds, as important structural skeletons, widely exist in drug molecules and biologically active molecules. At present, the most commonly used method is to use POBr at high temperature with aminopyridine or quinoline as raw material 3 or Br 2 bromination reaction. [0003] However, the regional control of the existing preparation methods mainly depends on the substrate, and has side reactions such as debrominated products and over-brominated. [0004] In view of this, the present invention is proposed. Contents of the invention [0005] The purpose of the present invention is to provide a method and application of bromination reaction of nitrogen-containing heterocyclic compounds, aiming at in...

Claims

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Application Information

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IPC IPC(8): C07D215/18C07D213/61
CPCC07D215/18C07D213/61
Inventor 付海燕陈华李顺郑学丽李瑞祥袁茂林
Owner SICHUAN UNIV
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