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Bifunctional 4-TMS-5-I-1,2,3-triazole compound as well as preparation method and application thereof

A 4-TMS-5-I-1, -5-I-1 technology, applied in the field of synthesizing 1,2,3-triazole compound intermediates substituted by 5-position heteroatoms, can solve the problem of expensive transition metals Catalysts and reaction substrates are limited in choice and cannot be used to provide other problems, achieving the effects of low price, simple preparation, and avoiding reaction conditions

Inactive Publication Date: 2015-05-06
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with the CuAAC reaction, these methods require expensive transition metal catalysts, the choice of reaction substrates is very limited, and the reaction conditions are relatively harsh.
More importantly, triazoles substituted with heteroatoms at position 5 are widely used in bioactive molecules, and the above methods cannot be used to provide 1,2,3-triazoles with heteroatoms at positions 5

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 10ml round-bottomed flask, add 1mmol benzyl azide, 1.2mmol trimethylsilyl acetylene, 1.2mmol DIPEA, 1.2mmol cuprous iodide and 1.2mmol NCS in sequence and mix and stir for 12 hours at room temperature. The reaction process was analyzed by TLC monitor. After the reaction was completed, it was extracted with ethyl acetate, and the organic phase was washed and separated by silica gel column chromatography to obtain the pure product of the target product with a yield of 85%. The product was a light brown solid with a melting point of 96-98°C. 1 H NMR (CDCl 3 , 400 MHz): δ 7.36-7.28 (m, 5 H), 5.62 (s, 2H), 0.40 (s, 9 H). 13 C NMR (CDCl 3 , 101 MHz): δ 133.7, 127.9, 127.4, 127.3, 126.9, 83.7, 52.6, -0.9, -2.23. HRMS (ESI) m / z calculate for (M+H + ) C 12 h 17 IN 3 Si + : 358.0236, Found: 358.0231, calculate for (M+Na + ) C 12 h 16 IN 3 NaSi + : 380.0050, Found: 380.0052.

Embodiment 2

[0034] In a 10ml round bottom flask, add 1mmol p-methoxybenzyl azide, 1.2mmol trimethylsilyl acetylene, 1.2mmol DIPEA, 1.2mmol cuprous iodide and 1.2mmol NCS in turn, and mix and stir for 12 hours at room temperature. The reaction process was monitored by TLC. After the reaction was finished, it was extracted with ethyl acetate, the organic phase was cleaned, and the pure product of the target product was obtained by silica gel column chromatography, with a yield of 83%, and the product was a viscous liquid. 1 H NMR (400 MHz, CDCl 3 ) δ 7.34-7.12 (m, 2H), 6.85 (d, J = 8.5 Hz, 2H), 5.52 (d, J = 16.2 Hz, 2H), 3.78 (s, 3H), 0.38 (s, 7H), 0.25 (s, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ 159.6, 151.2, 129.5, 126.6, 125.9, 114.2, 84.4, 77.4, 77.1, 76.8, 55.3, 54.3, 53.1. HRMS (ESI) m / z calculate for (M+H + ) C 13 h 19 IN 3 OSi + : 388.0337, Found: 388.0336.

Embodiment 3

[0036] In a 10ml round bottom flask, add 1mmol anthracenemethyl azide, 1.2mmol trimethylsilyl acetylene, 1.2mmol DIPEA, 1.2mmol cuprous iodide and 1.2mmol NCS in turn and mix and stir for 12 hours at room temperature. The reaction process uses TLC monitoring. After the reaction was finished, it was extracted with ethyl acetate, the organic phase was cleaned, and the pure product of the target product was obtained by silica gel column chromatography, with a yield of 81%, and the product was a viscous liquid. 1 H NMR (400 MHz, CDCl 3 ) δ 7.73 (s, 1H), 7.24 (d, J = 2.1 Hz, 1H), 6.92-6.81 (m, 2H), 5.54 (s, 2H), 3.79 (s, 3H), 0.07 (s, 3H) . 13 C NMR (101 MHz, CDCl 3 ( + ) C 20 h 21 IN 3 Si + : 458.0544, Found: 458.0551.

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PUM

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Abstract

The invention discloses a bifunctional 4-TMS-5-I-1,2,3-triazole compound as well as a preparation method and application thereof. According to the technical scheme, the bifunctional 4-TMS-5-I-1,2,3-triazole compound is characterized by being prepared at normal temperature, wherein trimethyl silyl acetylene and nitrine serve as raw materials, acetonitrile serves as a solvent, cuprous iodide serves as a catalyst, N-chlorosuccinimide serve as an oxidant, and N-di(isopropyl)ethylamine serves as an alkali. The bifunctional 4-TMS-5-I-1,2,3-triazole compound has a structural formula as shown in the specification, wherein R is as shown in the specification. The invention further discloses a preparation method of the bifunctional 4-TMS-5-I-1,2,3-triazole compound and a method of further synthesizing a 1,5-di-substituted-1,2,3-triazole compound from the bifunctional 4-TMS-5-I-1,2,3-triazole compound which serves as an intermediate. The raw materials are wide in source, are easy to prepare and are low in cost, and the cuprous iodide adopted by reaction serves as the catalyst and the reactant, is very low in cost, is simple and is easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of synthesizing 1,2,3-triazole compound intermediates substituted by 5-position heteroatoms, and specifically relates to a bifunctional 4-TMS-5-I-1,2,3-triazole compound Compounds and their preparation and applications. Background technique [0002] As a pharmacophore and functional structure, 1,2,3-triazole has a wide range of applications in medicine, pesticides, dyes, chiral catalysis, etc. Therefore, many people have done a lot of research work on the modification and derivatization of the 1,2,3-triazole structure. Since the Sharpless and Medal working groups respectively reported that azide and terminal alkynes can generate triazole five-membered rings (CuAAC reaction) under the catalysis of copper in 2002, a large number of CuAAC reactions have been synthesized under the conditions of different copper catalysts and solvents1 ,4 disubstituted 1,2,3-triazoles have been reported one after another. Howe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07D249/06C07D249/04
Inventor 李凌君朱安莲尚同鹏马晓南郭海云
Owner HENAN NORMAL UNIV
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