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Nitro-substituted azacyclopropene compound and preparation method thereof

A nitrogen heterocycle and compound technology, applied in the field of organic synthesis methodology, can solve problems such as functional group tolerance under harsh reaction conditions, achieve good substrate applicability and functional group tolerance, mild reaction conditions, and simple process conditions. Effect

Inactive Publication Date: 2020-06-05
南京康立瑞生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in many cases, currently known methods still suffer from some limitations, such as the use of stoichiometric transition metals, harsh reaction conditions and limited functional group tolerance

Method used

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  • Nitro-substituted azacyclopropene compound and preparation method thereof
  • Nitro-substituted azacyclopropene compound and preparation method thereof
  • Nitro-substituted azacyclopropene compound and preparation method thereof

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preparation example Construction

[0026] A preparation method of a nitro-substituted aziridine compound, comprising the following steps:

[0027] Step 1: Under the condition of inert gas protection, mix 0.10mmol nitroxime, 0.0025mmol [RhCp*Cl 2 ] 2 , 0.15mmol quinidine, and then add 1-2mL ultra-dry 1,2-dichloroethane solvent to obtain a reaction solution, stir the reaction at 25°C, and monitor the reaction through a TLC plate.

[0028] Step 2: After the reaction is completed, the insoluble solid is removed by filtration, the obtained solution is concentrated under reduced pressure to remove the solvent, and then purified by column chromatography to obtain the target product nitro-substituted aziridine compound.

[0029] Further, in step one, the inert gas is nitrogen.

[0030] Further, in step one, nitroxime, [RhCp*Cl 2 ] 2 , The molar ratio of quinidine mixed is 1:0.025:1.5.

[0031] Further, in step 2, when column chromatography is used for purification, the adsorbent is 200-300 mesh silica gel powder, ...

Embodiment

[0033] S1: In inert gas N 2 Under protected conditions, 0.10mmol nitroxime, 0.0025mmol [RhCp*Cl 2 ] 2 , 0.15mmol quinidine, and then add 1-2mL ultra-dry 1,2-dichloroethane solvent to obtain a reaction solution, stir the reaction at 25°C, and monitor the reaction through a TLC plate.

[0034] S2: After the reaction is completed, the insoluble solid is removed by filtration, the obtained solution is concentrated under reduced pressure to remove the solvent, and then purified by column chromatography to obtain the target product nitro-substituted aziridine compound.

[0035] The obtained target product was detected, and the results were as follows: figure 1 , 2 as shown, figure 1 2-Nitro-3-phenyl-2H-azacyclopropene product 1 H NMR spectrum, figure 2 2-Nitro-3-phenyl-2H-azacyclopropene product 13 C NMR spectrum.

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Abstract

The invention particularly relates to a nitro-substituted azacyclopropene compound and a preparation method thereof. The method comprises the following steps: mixing 0.10 mmol of nitrooxime, 0.0025 mmol of [RhCp*Cl2] 2 and 0.15 mmol of quinidine under the condition of inert gas protection, then adding 1-2 mL of a super dry 1,2-dichloroethane solvent to obtain a reaction solution, carrying out a stirring reaction at 25 DEG C, and monitoring the reaction through a TLC plate; and after the reaction is finished, filtering to remove insoluble solids, carrying out reduced pressure concentration on the obtained solution to remove the solvent, and purifying the solution by column chromatography to obtain the target product nitro-substituted azacyclopropene compound. The preparation method providedby the invention has the advantages of simple process conditions and mild reaction conditions, and can effectively obtain the nitro-substituted azacyclopropene compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis methodology, in particular to a nitro-substituted aziridine compound and a preparation method thereof. Background technique [0002] Azacyclopropene, the smallest unsaturated nitrogen-containing heterocyclic ring structure, has two carbon atoms and a C=N bond in the three-membered ring, and widely exists in many natural products and drug molecules. [0003] [0004] Aziridines can be conveniently further derivatized due to their unique structures and high chemical reactivity. As a result, aziridine derivatives have attracted widespread attention in the biological and organic chemistry community, prompting synthetic chemists to explore various ways to construct them. So far, many methods for synthesizing 2H-aziridine compounds have been developed. Among these reported methods, the Neber reaction is the most straightforward method for the synthesis of aziridines. [0005] However, in...

Claims

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Application Information

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IPC IPC(8): C07D203/04C07D203/02
CPCC07D203/02C07D203/04
Inventor 吴荣
Owner 南京康立瑞生物科技有限公司