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N2-alkenyl benzotriazole derivative and synthetic method thereof

A technology for alkenyl benzotriazoles and a synthesis method, which is applied in the field of N2-alkenyl benzotriazole derivatives and the synthesis thereof, can solve the problems of reducing the aromaticity of benzotriazoles and the like, and achieves simple and mild reaction conditions. , The effect of strong reaction universality and high yield

Active Publication Date: 2019-01-04
ZHOUKOU NORMAL UNIV +1
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  • Claims
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Problems solved by technology

However, with N 1 - substituted benzotriazole compared to the N of benzotriazole due to 2 - The aromaticity of the isomer is reduced, making the selectivity of benzotriazole N 2 - Functionalization has become a very challenging task, which also limits the application of such derivatives in different fields

Method used

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  • N2-alkenyl benzotriazole derivative and synthetic method thereof
  • N2-alkenyl benzotriazole derivative and synthetic method thereof
  • N2-alkenyl benzotriazole derivative and synthetic method thereof

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preparation example Construction

[0023] N as above 2 - the synthetic method of alkenyl benzotriazole derivatives, concrete steps are as follows: in solvent I, in catalyst M (OTf) n Under the catalysis of benzotriazole, iodine source and olefin react at room temperature for 0.5-5h, after concentration, add solvent II and base, react at 50-70°C for 8-15h, and get the target after concentration and column chromatography compound.

[0024] Solvent I is chloroform, dichloromethane, dichloroethane, ethyl acetate or 1,4-dioxane.

[0025] Catalyst M(OTf) n is Zn(OTf) 2 , Cu(OTf) 2 or Al(OTf) 3 .

[0026] Catalyst M(OTf) n The number of moles is 2-10% of the number of moles of benzotriazole.

[0027] The base is potassium tert-butoxide, sodium tert-butoxide, sodium hydride, potassium carbonate or sodium carbonate.

[0028] The molar number of base is 2-5 times of that of benzotriazole.

[0029] The molar ratio of benzotriazole, iodine source and alkene is 1:(1-2):(1-3).

[0030] The iodine source is N-iodos...

Embodiment 1

[0043] With chloroform as solvent, 0.05mol Zn(OTf) 2 As a catalyst, 1.0mol benzotriazole, 1.5mol N-iodosuccinimide and 2.0mol styrene were reacted at room temperature for 1 hour, then concentrated, using methanol as solvent, 5.0mol potassium carbonate as base, 60°C After reacting for 12h, the target compound A can be obtained through concentration and column chromatography, and the yield is 81%, N 2 - 95% selectivity.

[0044] 1 H NMR (400MHz, CDCl 3 ):δ7.94-7.89(m,2H),7.47-7.41(m,7H),6.21(s,1H),5.67(s,1H); 13 C NMR (100MHz, CDCl 3 ): δ147.2, 144.7, 134.6, 129.6, 128.5, 128.3, 127.3, 118.5, 111.1.

Embodiment 2

[0046] Its specific synthetic steps refer to Example 1, and the olefin is 4-tert-butylstyrene.

[0047] B yield is 90%, N 2 - 99% selectivity.

[0048] 1 H NMR (400MHz, CDCl 3 ):δ7.95-7.90(m,2H),7.46(d,J=8.5Hz,2H),7.43-7.41(m,2H),7.39(d,J=8.4Hz,2H),6.15(s, 1H), 5.65(s, 1H); 13 C NMR (100MHz, CDCl 3 ): δ152.7, 147.1, 144.7, 131.7, 127.9, 127.2, 125.5, 118.5, 110.6, 34.8, 31.3.

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Abstract

The invention provides a N2-alkenyl benzotriazole derivative which is a compound as shown in a formula. A synthetic method comprises the following steps: carrying out a reaction among benzotriazole, N-iodosuccinimide and olefin at a room temperature for 0.5-5 hours by taking chloroform as a solvent and M(OTf)n as a catalyst; then carrying out condensation; carrying out a reaction at 50-70 DEG C for 8-15 hours by taking methanol as a solvent to obtain the target product. The method has the obvious characteristic that the reaction conditions are simple and mild, no transitional metals participate in the reaction and the yield and N2-selectivity are relatively high. At present, no method of constructing N2-alkenyl benzotriazole directly by means of a one-pot method is reported, and the synthetic method is quite simple and cheap and simple to operate, achieves the N2-selectivity which is over 84%, and is high in reaction universality.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to N 2 -Alkenyl benzotriazole derivatives and synthesis method thereof. Background technique [0002] N-substituted benzotriazole derivatives have wide application value in the fields of organic synthetic chemistry, material science and medicinal chemistry. due to N 2 -Substituted benzotriazoles have received great attention due to their broad spectrum of biological activities. However, with N 1 - substituted benzotriazole compared to the N of benzotriazole due to 2 - The aromaticity of the isomer is reduced, making the selectivity of benzotriazole N 2 -Functionalization has become a very challenging task, which also limits the application of such derivatives in different fields. Contents of the invention [0003] The present invention provides a kind of N 2 -Alkenyl benzotriazole derivatives and synthesis method thereof. [0004] The purpose of the present inve...

Claims

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Application Information

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IPC IPC(8): C07D249/18C07D249/20
CPCC07D249/18C07D249/20
Inventor 朱莉莉张辉田丽芳王亚辉
Owner ZHOUKOU NORMAL UNIV
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