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A kind of oxyallylamine compound and its preparation method and application

A technology of oxalylamine and heteroallylamine, which is applied in the field of oxalylamine compounds and their preparation, can solve the problem that the synthesis methods of oxalylamine compounds are few and do not conform to green chemistry Problems such as development concept and limited applicability of substrates, to achieve the effect of novel and efficient synthetic methods, wide applicability of substrates, and high utilization rate of atoms

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although the synthesis strategy of allylamine compounds is very mature, there are very few synthetic methods for oxyallylamine compounds. Among the currently known methods, it can be obtained by the reaction of phenyl allenyl ether and morpholine Corresponding oxyallylamine compounds, but the selectivity of the reaction is very poor, the yield is not high, and the substrate applicability is limited, which makes the conversion efficiency of the reaction low, does not have broad application prospects, and does not In line with the development concept of green chemistry

Method used

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  • A kind of oxyallylamine compound and its preparation method and application
  • A kind of oxyallylamine compound and its preparation method and application
  • A kind of oxyallylamine compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 2

[0066] In the sealed tube, firstly add 0.01 mmol copper acetate, 0.01 mmol zinc chloride dissolved in 1.0 ml dichloromethane solvent, and finally add 0.2 mmol N-methyl-1-naphthylamine and 0.3 mmol phenyl Allenyl ether was stirred and reacted at 700 rpm at 50 degrees Celsius for 6 hours, and the stirring was stopped. 5 mL of water was added, extracted three times with ethyl acetate, the organic phases were combined and dried over 0.5 g of anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated and purified by thin layer chromatography to obtain the target product. The developing agent is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 200:1, and the yield is 82%.

[0067] The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows image 3 and Figure 4 shown; the structural characterization data is as follows:

[0068] 1 H NMR (400MHz, CDCl 3 )δppm 8.37-8.22(m, 1H), ...

Embodiment 3

[0075] In the sealing tube, firstly add 0.01 mmol copper acetate, 0.01 mmol zinc chloride dissolved in 1.0 ml dichloromethane solvent, and finally add 0.2 mmol N-allylaniline and 0.3 mmol phenyl allene ether , the reaction was stirred at 50 degrees Celsius at 700 rpm for 6 hours, and the stirring was stopped. 5 mL of water was added, extracted three times with ethyl acetate, the organic phases were combined and dried over 0.5 g of anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated and purified by thin layer chromatography to obtain the target product. The developing agent was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 200:1, and the yield was 81%. The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows Figure 5 and Image 6 shown; the structural characterization data is as follows:

[0076] 1 H NMR (400MHz, CDCl 3 )δppm 7.32(t, J=8.0Hz, 2H), 7.19(t, J=...

Embodiment 4

[0083] In the sealing tube, firstly add 0.01 mmol copper acetate, 0.01 mmol zinc chloride dissolved in 1.0 ml dichloromethane solvent, and finally add 0.2 mmol 2,4-dichloroaniline and 0.3 mmol phenylene ether, the reaction was stirred at 50 degrees Celsius at 700 rpm for 6 hours, and the stirring was stopped. 5 mL of water was added, extracted with ethyl acetate 3 times, the organic phases were combined and dried over 0.5 g of anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated and purified by thin layer chromatography to obtain the target product. The developing agent is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 500:1, and the yield is 70%.

[0084] The hydrogen spectrogram and carbon spectrogram of the product obtained in this example are respectively as follows Figure 7 and Figure 8 shown; the structural characterization data is as follows:

[0085] 1 H NMR (400MHz, CDCl 3 )δppm 7.33(t, J=8.0Hz, 2H), 7.24(d...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses an oxalylamine compound, a preparation method and application thereof. Add copper salt catalyst and additives into the reactor, then add dissolved organic solvent, stir and react at 40-60°C, the reaction product is separated and purified to obtain oxalylamine compounds, the reaction formula of the above preparation method As shown in formula (I). The method of the present invention synthesizes a series of oxalylamine compounds with simple and easy-to-obtain allene ethers and amines as reaction raw materials. The method has the advantages of simple and easy-to-obtain raw materials, convenient operation, mild conditions, high atom utilization rate, and economical steps. High stability, wide substrate applicability, good functional group tolerance, etc.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an oxaallylamine compound and a preparation method and application thereof. Background technique [0002] Functionalized amines are ubiquitous in natural products, pharmaceuticals, and other small molecules with biological activity. Among them, oxalylamine compounds are key intermediates in the synthesis of drugs, which have attracted extensive attention of chemists in recent years. For example: (a) Pramocaine hydrochloride can reduce the permeability of nerve cell membranes to sodium ions, Blocks the generation and conduction of nerve impulses; (b) Propranolol is a non-selective β-adrenergic receptor (βAR) antagonist with high affinity for β1AR and β2AR with Ki values ​​of 1.8 nM and 0.8 nM, respectively. Propranolol inhibits [ 3 Binding of H]-DHA to rat meningeal preparations, IC 50 was 12nM. Propranolol is used in studies related to hypertension, pheo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/02C07C217/46C07D209/86C07D295/084C07D211/14
CPCC07C217/46C07C213/02C07D209/86C07D295/084C07D211/14
Inventor 江焕峰吴紫英伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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