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Synthetic method of alpha-hydroxyl alkenyl azide compound

A synthesis method and hydroxyalkene technology, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions, narrow substrate range, numerous steps, etc., and achieve the effects of simple steps, simple raw materials, and shortened reaction time.

Inactive Publication Date: 2015-06-17
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Targetedly solve the problems of narrow substrate range, low yield, harsh reaction conditions and numerous steps

Method used

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  • Synthetic method of alpha-hydroxyl alkenyl azide compound
  • Synthetic method of alpha-hydroxyl alkenyl azide compound
  • Synthetic method of alpha-hydroxyl alkenyl azide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 α-Hydroxyalkenyl Azide Derivatives 2a preparation of

[0026]

[0027] Add dimethyl sulfoxide (DMSO) (2 mL), 1-phenyl-2-proparg-1-ol to a 25 mL round bottom flask with a magnetic stirring device 1a (1 mmol), azidotrimethylsilane (TMSN 3 ) (1.5 mmol), put it in an 80°C oil bath, stir well, add silver carbonate (0.1 mmol), and continue stirring. The reaction time is 1h, at this time TLC detects the substrate 1a After disappearing, the reaction solution was poured into water (15 mL), extracted with dichloromethane (3 × 15 mL), and the organic phases were combined. Backwash with water (3 x 20 mL). The organic phase was dried with anhydrous magnesium sulfate, filtered with suction, and then evaporated under reduced pressure to remove the organic solvent, and finally subjected to silica gel column chromatography to obtain a yellow liquid 2a , confirmed by NMR to be α-hydroxyalkenyl azide derivatives 2a , and its yield is 85%.

[0028] Spectral analysis dat...

Embodiment 2

[0030] Example 2 α-Hydroxy alkenyl azide derivatives 2e preparation of

[0031] Replace the 1-phenyl-2-propargyl-1-alcohol in "Example 1" with 1-(p-chlorophenyl)-2-propargyl-1-alcohol, and the reaction conditions change the catalyst in "Example 1" to Silver nitrate (consumption is constant), temperature changes 25 ℃ into, and the reaction times is 8h, and other steps, consumption are all constant. The experimental results are shown in Table 1

[0032]

[0033] Spectral analysis data 2e :

[0034] 1 H-NMR (500 MHz, CDCl 3 ) δ 2.69 (s, 1H), 4.82-4.84 (m, 1H), 5.05 (s, 1H), 5.07-5.09 (m, 1H), 7.30-7.34 (m, 4H); 13 C-NMR (CDCl 3 , 125 MHz) δ 73.5, 98.9, 127.9, 128.6, 134.0, 138.4, 147.8.

Embodiment 3

[0035] Example 3 α-Hydroxyalkenyl Azide Derivatives 2h preparation of

[0036] With 1-(2-furyl)-2-proparg-1-ol instead of 1-phenyl-2-proparg-1-alcohol in "Example 1", the reaction conditions change "Example 1" catalyst into fluorine silver oxide, trimethylsilyl azide was changed to sodium azide, the solvent was changed to N,N -Dimethylformamide (DMF), the reaction time is 5h, and other steps and dosages remain unchanged. The experimental results are shown in Table 1.

[0037]

[0038] Spectral analysis data 2h :

[0039] 1 H-NMR (500 MHz, CDCl3) δ 2.55-2.73 (m, 1H), 4.88-4.91 (d, J = 1.0 Hz, 1H), 5.10-5.16 (m, 2H), 6.34-6.39 (m, 2H), 7.39- 7.42 (m, 1H); 13 C-NMR (CDCl3, 125 MHz) δ 68.2, 99.5, 107.9, 110.5, 142.7, 145.5, 152.6.

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Abstract

The invention relates to a synthetic method of alpha-hydroxyl alkenyl azide compound, and belongs to the technical field of organic synthetic chemistry. As alpha-hydroxyl alkenyl azide derivatives have particular reactivity, much attention has been paid to the synthesis and application of the alpha-hydroxyl alkenyl azide derivatives. The alpha-hydroxyl alkenyl azide derivatives are synthesis precursors of nitrogenous heterocyclic compounds. By utilizing propargyl alcohol which is simple, stable and easy to get and azide trimethyl silicane, the alpha-hydroxyl alkenyl azide compound can be compounded by one step; the synthetic method of the alpha-hydroxyl alkenyl azide compound has the characteristics that the operation is simple and efficient, the raw materials and reagents are stable and easy to get, and the product structure is stereospecific; the synthetic method is applicable to various alpha-hydroxyl alkenyl azide compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to a method of efficiently synthesizing a stereospecific α-hydroxyalkene in the next step of silver carbonate catalysis starting from simple and easy-to-obtain raw materials such as propynyl alcohol compounds and azidetrimethylsilane The method of base azides. technical background [0002] As a classic functionalized olefinic compound, alkenyl azide has very high reactivity and is widely used in the synthesis of nitrogen-containing compounds and peptides, and plays a pivotal role in the pharmaceutical, pesticide and dye industries. First of all, azide has the characteristics of 1,3-dipole, and can perform [3+2] ring closure reaction with unsaturated chemical bonds such as carbon-carbon double bonds, carbon-carbon triple bonds, and carbon-nitrogen triple bonds ( Chem. Rev. 2008, 108 , 2952-3015; Wiley & Sons: Chichester , 2010, 265-269), a series of five-member...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C247/10C07D307/52C07D333/20C07D203/02C07D203/08
Inventor 毕锡和刘振华
Owner NORTHEAST NORMAL UNIVERSITY
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