Method for simply preparing boron-nitrogen pyridine compound

A technology of borazine and compound, which is applied in the field of synthesizing borazine compounds, and achieves the effects of less by-products, low production cost and simple post-treatment

Pending Publication Date: 2022-07-12
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above synthetic methods have certain limitations in terms of raw material sources, functional group universality, and reaction substrates.

Method used

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  • Method for simply preparing boron-nitrogen pyridine compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 108.1 mg of phenylhydrazine, 70.1 mg of 2-methacrolein, 2 drops of glacial acetic acid and 40 mL of ethanol into a 100-mL round-bottomed flask equipped with a magnet, and heated at 85 °C for 3-6 h. After the reaction, the reaction solution was spin-dried , and the aryl hydrazone was obtained by column separation and purification. In a glove box, 247.7 mg of phenylboron dibromide and 15 mL of toluene were added to a 50 mL Shrek bottle containing a magnet and mixed well. 160.2 mg of the aryl hydrazone synthesized above, 158.2 mg of pyridine and 40 mL of toluene were added to a 100 mL Shrek bottle, and a dropping funnel device was installed. Transfer the toluene solution of phenylboron dibromide to a dropping funnel, slowly add dropwise to the mixture of aryl hydrazone and pyridine at 0 °C, slowly return to room temperature, install a heating reflux device, and fill it with argon. balloon connection. The reaction was heated at 110 °C for 8 hours. After the reaction w...

Embodiment 2

[0019] 223.5mg of 2-bromophenylhydrazine hydrochloride, 101.2mg of triethylamine, 70.1mg of 2-methacrolein, 2 drops of glacial acetic acid and 40mL of ethanol were added to a 100mL round-bottomed flask with a magnet, heated at 85°C for 3 -6h, after the reaction, the reaction solution was spin-dried, and the aryl hydrazone was obtained by column separation and purification. In a glove box, add 247.7 mg of phenylboron dibromide and 15 mL of toluene into a 50 mL Shrek bottle with a magnet and mix well. 239.1 mg of the aryl hydrazone synthesized above, 158.2 mg of pyridine and 40 mL of toluene were added to a 100 mL Shrek bottle, and a dropping funnel device was installed. Transfer the toluene solution of phenylboron dibromide to a dropping funnel, slowly add dropwise to the mixture of aryl hydrazone and pyridine at 0 °C, slowly return to room temperature, install a heating reflux device, and fill it with argon. balloon connection. The reaction was heated at 110° C. for 8 h. Aft...

Embodiment 3

[0023] 223.5mg of 4-bromophenylhydrazine hydrochloride, 101.2mg of triethylamine, 70.1mg of 2-methacrolein, 2 drops of glacial acetic acid and 40mL of ethanol were added to a 100mL round-bottomed flask with magnetron, heated at 85°C 3-6h, after the reaction, the reaction solution was rotated to dryness, and the aryl hydrazone was obtained by column separation and purification. In a glove box, add 247.7 mg of phenylboron dibromide and 15 mL of toluene into a 50 mL Shrek bottle with a magnet and mix well. 239.1 mg of the aryl hydrazone synthesized above, 158.2 mg of pyridine and 40 mL of toluene were added to a 100 mL Shrek bottle, and a dropping funnel device was installed. Transfer the toluene solution of phenylboron dibromide to a dropping funnel, slowly add dropwise to the mixture of aryl hydrazone and pyridine at 0 °C, slowly return to room temperature, install a heating reflux device, and fill it with argon. balloon connection. The reaction was heated at 110° C. for 8 ho...

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Abstract

The invention relates to the technical field of synthesis of boron-nitrogen-pyridine compounds, in particular to a simple preparation method of a boron-nitrogen-pyridine compound, which comprises the following steps: taking a phenylhydrazone derivative generated by reacting phenylhydrazine with different substituent groups with 2-methylacrolein as a reaction substrate, dissolving the reaction substrate, phenyl boron dibromide and pyridine in an organic solvent according to a ratio, and reacting under the protection of argon to obtain the boron-nitrogen-pyridine compound. Heating and stirring at 110 DEG C for 8 hours, pumping the organic solvent after the reaction is completed, and separating and purifying through a column to obtain the boron-nitrogen-pyridine compound. The method has the advantages of being wide in raw material source, low in price and easy to obtain, low in production cost, simple in reaction condition, easy to implement, good in functional group universality, few in by-product, simple in post-treatment and the like.

Description

technical field [0001] The invention relates to the technical field of synthesizing pyridine borazine compounds, in particular to a method for simply preparing pyridine borazine compounds. Background technique [0002] The boron nitrogen pyridine compound is a structural skeleton in the boron nitrogen heterocyclic ring system, and its composition is to replace the C=C bond in the pyridine ring with a B-N bond. At present, borazine compounds can be used in the field of biological research, such as antibacterial agents, chest muscle cell inhibitors, biological macromolecular markers, etc., and can also be used in the field of organic chemistry, such as synthetic building blocks in organic small molecules, chiral fluorescent molecular probes Such compounds have good optoelectronic properties and very broad application prospects. [0003] At present, there are four classical methods for synthesizing boron nitrogen pyridine compounds: ① o-formyl phenylboronic acid derivatives re...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 敬冰崔春明张建颖
Owner NANKAI UNIV
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