no 2 -Alkenyl benzotriazole derivatives and synthesis method thereof

A technology of alkenyl benzotriazoles and synthesis methods, which is applied in the field of N2-alkenyl benzotriazole derivatives and their synthesis, can solve the problems such as the reduction of benzotriazole aromaticity, and achieve simple and mild reaction conditions , The synthesis method is simple and cheap, and the effect of high yield

Active Publication Date: 2021-12-21
ZHOUKOU NORMAL UNIV +1
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  • Description
  • Claims
  • Application Information

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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

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  • no <sup>2</sup> -Alkenyl benzotriazole derivatives and synthesis method thereof
  • no <sup>2</sup> -Alkenyl benzotriazole derivatives and synthesis method thereof
  • no <sup>2</sup> -Alkenyl benzotriazole derivatives and synthesis 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

provided by the invention N 2 -Alkenyl benzotriazole derivatives are compounds such as formula I:, with chloroform as solvent, M(OTf) n As a catalyst, react benzotriazole, N-iodosuccinimide and olefin at room temperature for 0.5-5h, then concentrate, use methanol as solvent and potassium carbonate as base, react at 50-70°C for 8-15h, The target compound can be obtained. A notable feature of this method is that the reaction conditions are simple and mild, no transition metals are involved, and the yield and N 2 ‑ Higher selectivity. Currently, the one-pot method directly builds N 2 The method of ‑alkenylbenzotriazole has not yet been reported, and the synthetic method is very simple and cheap, and is easy to operate and has reached more than 84%. N 2 ‑Selectivity, strong universality of response.

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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Patent Type & Authority Patents(China)
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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