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Synthetic method for preparing large quantities of α-vinyl azides

A synthetic method and azide technology, applied in organic chemical methods, thioether preparation, sulfonamide preparation, etc., can solve problems such as difficulties in industrial production, harsh reaction conditions, narrow substrate range, etc., and facilitate modification and application , short reaction time, easy process effect

Active Publication Date: 2020-09-15
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the reported methods for the synthesis of alkenyl azides have relatively narrow substrate scope, low yield, harsh reaction conditions, and many steps, which have brought many difficulties to industrial production.

Method used

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  • Synthetic method for preparing large quantities of α-vinyl azides
  • Synthetic method for preparing large quantities of α-vinyl azides
  • Synthetic method for preparing large quantities of α-vinyl azides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of α-vinyl azide compound 2a

[0028]

[0029] To a 100 mL round bottom flask equipped with a 3 cm oval magnetic stir bar was added p-tolueneacetylene 1a (50 mmol) followed by dimethyl sulfoxide (DMSO) (50 mL). Then trimethylsilyl azide (75 mmol) and water (100 mmol) were added thereto via a 10 mL syringe. Finally, newly prepared white silver azide (2.5 mmol) was added thereto, and stirred evenly under air condition. Subsequently, the flask was placed in an oil bath at a temperature of 80° C. for the reaction. After 100 min, TLC detected that the substrate disappeared. The round bottom flask was taken out from the oil bath, and after the reaction was cooled to room temperature, the dark brown solution was transferred to a 250 mL beaker, and 80 mL of dichloromethane and 100 mL of water were added thereto for extraction. And the upper aqueous phase was continuously extracted with 50 mL of dichloromethane, and this was repeated three to five times. The o...

Embodiment 2

[0034] Preparation of α-vinyl azide compound 2b

[0035]

[0036] Phenylacetylene 1b was used to replace p-tolueneacetylene 1a in "Example 1", the reaction conditions were changed to 120 min in the reaction time of "Example 1", and other steps and dosages were unchanged. The experimental results are shown in Table 1.

[0037] Spectrum Analysis Data 2b(C 8 h 7 N 3 )

[0038] 1 H NMR (600MHz, CDCl 3 )δ7.61-7.55(m,2H),7.39-7.34(m,3H),5.44(d,J=2.4Hz,1H), 4.97(d,J=2.4Hz,1H);

[0039] 13 C NMR (150MHz, CDCl 3 )δ145.04, 134.26, 129.08, 128.42, 125.54, 97.95.

Embodiment 3

[0041] Preparation of α-vinyl azide compound 2c

[0042]

[0043] Replace p-tolylacetylene 1a in "Example 1" with p-chlorophenylacetylene 1c, and the reaction conditions change the reaction times into 80min in "Example 1", and other steps and consumption are all constant. The experimental results are shown in Table 1.

[0044] Spectrum Analysis Data 2c(C 8 h 6 ClN 3 )

[0045]1 H NMR (600MHz, CDCl 3 )δ7.49(d, J=8.4Hz, 2H), 7.32(d, J=9.0Hz, 2H), 5.43(d, J=3.0Hz, 1H), 4.97(d, J=2.4Hz, 1H) ;

[0046] 13 C NMR (150MHz, CDCl 3 )δ144.08, 135.03, 132.73, 128.61, 126.83, 98.13.

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Abstract

The invention relates to a synthesis method for preparing a large amount of alpha-vinyl azide compounds, and belongs to the technical field of organic synthesis chemistry. In the prior art, alpha-vinyl azide compounds have unique reactivity, the synthesis and the applications of the alpha-vinyl azide compounds are important, and the alpha-vinyl azide compounds have good application prospects in the field of organic synthesis. According to the present invention, a large amount of stereospecific alpha-vinyl azide compounds are subjected to one-step efficient synthesis by using the simple and easily-available raw material acetylene-based compound and the azidotrimethylsilane; the synthesis method has advantages of simple and easily-available raw materials, wide application, low catalyst consumption, batch synthesis, simple operation method and efficient reaction, and is suitable for synthesis of a large amount of alpha-vinyl azide compounds; and the product has the stereospecific structure.

Description

Technical field: [0001] The invention belongs to the technical field of organic synthesis chemistry, and the invention relates to a method of starting from the simple and easy-to-obtain raw material terminal alkyne compounds and azidotrimethylsilane in the next step of silver azide catalysis, which is highly efficient and a large amount of stereospecific synthesis method for α-vinyl azides. [0002] technical background: [0003] Since the alkenyl azide reported by Forster and Newman in 1910, alkenyl azide, as a classic functionalized olefinic compound, has very high reactivity and has been widely used in the synthesis of nitrogen-containing compounds. It plays a pivotal role in the pharmaceutical, pesticide and dye industries. First of all, azide has the characteristics of 1,3-dipole, and can carry out [3+2] ring closure reaction with unsaturated chemically bonded carbon-carbon double bond, carbon-carbon triple bond, and carbon-nitrogen triple bond (Chem.Rev.2008, 108,2952...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C247/10C07C247/08C07C319/20C07C323/32C07C303/40C07C311/18
CPCC07B2200/07C07C247/08C07C247/10C07C303/40C07C319/20C07C323/32C07C311/18
Inventor 毕锡和季庆贺曹姗姗
Owner NORTHEAST NORMAL UNIVERSITY
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