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A kind of preparation method of α-azide aryl ketone derivative

A technology for azide aryl ketone and derivatives, which is applied in the field of preparation of α-azide aryl ketone derivatives, can solve the problems of reporting alkene azide/oxidation reaction methods and the like, and achieves the effects of simple operation and easy purification

Active Publication Date: 2021-09-03
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as the inventor knows, there is no prior art report on the azidation / oxidation reaction method of olefins without transition metal catalysts and harmful oxidant systems in the aqueous phase

Method used

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  • A kind of preparation method of α-azide aryl ketone derivative
  • A kind of preparation method of α-azide aryl ketone derivative
  • A kind of preparation method of α-azide aryl ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] To a Schlenk bottle was added the olefin of formula 1a (41.6 mg, 0.4 mmol), azidotrimethylsilane (TMSN 3 , 138.0 mg, 1.2 mmol), di-tert-butyl peroxide (DTBP, 116.8 mg, 0.8 mmol), and then added solvent water (H 2 0, 2mL), then the reactor was stirred and reacted under an oxygen atmosphere, 25 ° C, the reaction progress was monitored by TLC until the raw materials disappeared (the reaction time was 36 hours), after the reaction was completed, the reaction solution was extracted three times with ethyl acetate, The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (eluting solvent: ethyl acetate / n-hexane) to obtain the target product I-1. (26% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.92-7.90(m, 2H), 7.63(t, J=7.0Hz, 1H), 7.50(t, J=7.5Hz, 2H), 4.57(s, 2H); 13 C NMR (125MHz, CDCl 3 )δ: 193.2, 134.4, 134.2, 129.0, 127.9, 54.9.

Embodiment 2

[0035] silver carbonate (Ag 2 CO 3 , 219.1 mg, 0.8 mmol) instead of di-tert-butyl peroxide, and other conditions were the same as in Example 1, and the yield of the target product I-1 was 63%.

Embodiment 3

[0037] With the oxidizing agent iodobenzene acetate (PhI(OAc) 2 , 257.4 mg, 0.8 mmol) instead of di-tert-butyl peroxide, and other conditions were the same as in Example 1, and the yield of the target product I-1 was 47%.

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Abstract

The present invention relates to a kind of preparation method of α-azide aryl ketone derivative, this method is by adding substituted styrene, azidotrimethylsilane and oxidizing agent in Schlenk reaction bottle, then add water as solvent again, at a certain temperature , stirring and reacting under an oxygen atmosphere to obtain the azidation / oxidation product α-azide aryl ketone derivative.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a preparation method of an α-azidoarylketone derivative. Background technique [0002] α-Azidoarylketone derivatives are an important class of organic synthesis intermediates. On the one hand, they can further construct nitrogen heterocyclic compounds such as triazoles and aziridines with various biological activities. On the other hand, they can be converted into biologically active compounds. Key skeleton α-amino alcohol compounds with important application value in chemistry. Therefore, the development of economical and efficient methods for synthesizing α-azidoarylketone derivatives has attracted extensive attention of chemists. [0003] The inventors found that the synthetic methods for synthesizing and preparing α-azido aryl ketone derivatives in the prior art mainly include the following two: one is the nucleophilic substitution of α-halogenated aryl ketones...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C247/10
Inventor 魏文廷包雯慧孟潇潇孟亚楠
Owner NINGBO UNIV
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