Halogenated oxaallylamine compound as well as preparation method and application thereof

A technology of halogenated oxalylamine and heteroallylamine, which is applied in the field of halogenated oxalylamine compounds and their preparation, can solve the problem of no application prospect, limited substrate applicability, Problems such as halogenated oxalylamine cannot be applied to achieve the effect of novel and efficient synthesis method, wide substrate applicability, and mild conditions

Active Publication Date: 2021-03-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned reactions cannot be applied to the synthesis of halogenated oxyallylamines, which limits the substrate applicability of the reaction and does not have broad application prospects.

Method used

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  • Halogenated oxaallylamine compound as well as preparation method and application thereof
  • Halogenated oxaallylamine compound as well as preparation method and application thereof
  • Halogenated oxaallylamine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0063] In the test tube, first add 0.12 mmol of copper chloride in sequence, dissolve it in 1.0 ml of 1,4-dioxane solvent, and finally add 0.2 mmol of 2-methyl-N-methylaniline and 0.3 mmol of phenyl Allene ether was covered with an oxygen balloon, stirred and reacted at 40 degrees Celsius at 700 rpm for 6 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 500:1, and the yield is 82%.

[0064] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 and Figure 4 shown; the structural characterization data are shown below:

[0065] 1 H NMR (...

Embodiment 3

[0072] In the test tube, first add 0.12 mmol of copper chloride in sequence, dissolve it in 1.0 ml of 1,4-dioxane solvent, and finally add 0.2 mmol of 2-bromo-N-methylaniline and 0.3 mmol of phenyl bismuth Diene ether was covered with an oxygen balloon, stirred and reacted at 40 degrees Celsius at 700 rpm for 6 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 500:1, and the yield is 68%.

[0073] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 and Figure 6 shown; the structural characterization data are shown below:

[0074] 1 ...

Embodiment 4

[0081] In the test tube, first add 0.12 mmol of copper chloride in sequence, dissolve it in 1.0 ml of 1,4-dioxane solvent, and finally add 0.2 mmol of 4-methyl-N-methylaniline and 0.3 mmol of phenyl Allene ether was covered with an oxygen balloon, stirred and reacted at 40 degrees Celsius at 700 rpm for 6 hours, and then stopped stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by thin-layer chromatography to obtain the target product, the thin-layer chromatography used The developer is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 500:1, and the yield is 68%.

[0082] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 7 and Figure 8 shown; the structural characterization data are shown below:

[0083] 1 H NMR ...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a halogenated oxaallylamine compound as well as a preparation method and application thereof. The preparation method comprises the following steps: adding copper halide into a reactor, then adding an organic solvent, conducting dissolving, conducting stirring and reacting at 35-45 DEG C, and separating and purifying the reaction product to obtain the halogenated oxaallylamine compound. The reaction formula of the preparation method is as shown in a formula (I). According to the method, allene ether and aromatic amine which are simple and easy to obtain are used as reaction raw materials to synthesize a series of halogenated oxaallylamine compounds, and the method has the characteristics of simple and easy-to-obtain raw materials, convenience in operation, mild conditions, high step economy, wide substrate applicability, good functional group tolerance and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a halogenated oxalylamine compound and a preparation method and application thereof. Background technique [0002] Amines containing multiple heteroatoms are ubiquitous in natural products, drugs, and other small molecules with biological activity. Among them, allylamine compounds containing multiple heteroatoms are key intermediates in the synthesis of drugs, and have attracted widespread attention from chemists in recent years. For example: (a) Oxprenolol hydrochloride (Ba 39089) is an orally effective β-adrenergic receptor (β-AR) antagonist, Ki is 7.10nM; (b) Propranolol is a non-selective β-adrenergic receptor (βAR) antagonist with high affinity for β1AR and β2AR, Ki value 1.8nM and 0.8nM, respectively. Propranolol inhibits [ 3 Binding of H]-DHA to rat meningeal preparations, IC 50 is 12nM. Propranolol is used in studies related to hypertension, phe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/46C07C217/48C07C213/02C07C213/10
CPCC07C213/02C07C213/10C07C217/46C07C217/48
Inventor 江焕峰吴紫英伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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