Synthetic method of NH-1,2,3-triazole bipyridine compounds

A technology of triazole bipyridine and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of many steps, difficult synthesis, complicated operation and the like, and achieves the effects of mild reaction conditions, shortened synthesis route and wide range of substrates

Inactive Publication Date: 2016-05-04
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has some disadvantages: one is that the yield of synthetic pyridyl unsaturated nitro compounds is low and it is not easy to preserve; the other is that nitroolefins are prone to polymerization during the reaction, which greatly reduces the yield of the reaction; The price is relatively expensive, and the dosage reaches 20% mol
Thi

Method used

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  • Synthetic method of NH-1,2,3-triazole bipyridine compounds
  • Synthetic method of NH-1,2,3-triazole bipyridine compounds
  • Synthetic method of NH-1,2,3-triazole bipyridine compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of 4-(2-pyridyl)-2H-1,2,3-triazole:

[0020] The reaction formula is:

[0021]

[0022] The specific steps are: add 0.33mmol 2-pyridinecarbaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.04mmol AlCl to a 50mL round bottom flask 3 , 2mLDMSO, magnetically stirred and reacted at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:3 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 86%.

[0023] The proton nuclear magnetic spectrogram result of gained product is: 1 HNMR (600MHz, CDCl 3 ): δ7.97(s, 1H), 7.51(d, J=1.2Hz, 1H), 6.85(d, J=3.3Hz, 1H), 6.51(m, 1H). The result of NMR spectrum is: 13 CNMR (150MHz, CDCl 3 ): δ145.3, 142.8, 111.6, 107.8....

Embodiment 2

[0025] Synthesis of 4-(3-pyridyl)-2H-1,2,3-triazole:

[0026] The reaction formula is:

[0027]

[0028] The specific steps are: add 0.33mmol 3-pyridinecarbaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.04mmol AlCl to a 50mL round bottom flask 3 , 2mLDMSO, magnetically stirred and reacted at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:3 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 91%.

[0029] The proton nuclear magnetic spectrogram result of gained product is: 1 HNMR (500MHz, CDCl 3 -DMSO-d6)d=9.06(s,1H),8.57(s,1H),8.15-8.14(d,J=2.0Hz,1H),7.99(d,J=1.8Hz,1H),7.41-7.38 (m,1H).

Embodiment 3

[0031] Synthesis of 4-(4-pyridyl)-2H-1,2,3-triazole:

[0032] The reaction formula is:

[0033]

[0034] The specific steps are: add 0.33mmol 4-pyridinecarbaldehyde, 0.50mmol nitromethane, 0.39mmol sodium azide, 0.04mmol AlCl to a 50mL round bottom flask 3 , 2mLDMSO, magnetically stirred at 80°C for 12 hours, then extracted the reaction solution with ethyl acetate, washed the organic layer with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain the crude product. Ethyl acetate / petroleum ether=1:3 (V / V) was used as the eluent for column separation and purification to obtain the desired product, which was a white solid with a yield of 80%.

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Abstract

The invention relates to a novel synthetic method of NH-1,2,3-triazole bipyridine compounds. According to the methods, pyridinecarboxaldehyde, nitroalkane, sodium azide and a catalyst are sequentially added to a reaction solvent in a reaction container, the materials are stirred in the air under a heating condition and react, and the NH-1,2,3-triazole bipyridine compounds are prepared. The method has the benefits as follows: cheap and available AlCl3 is taken as the catalyst, aromatic aldehyde, nitroalkane and sodium azide have a one-pot reaction, the reaction conditions are mild, the yield is high, the raw materials are available, and the NH-1,2,3-triazole bipyridine compounds are synthesized conveniently and effectively.

Description

technical field [0001] The invention relates to a new synthesis method of NH-1,2,3 triazole bipyridine. technical background [0002] Polymeric complexes containing polyazole ligands have various structures and have potential application prospects in the fields of polymeric materials, catalytic materials, biological materials, and optical materials. In recent years, the research on the synthesis and application of multimeric complexes containing polyazole ligands has been extremely active. [0003] In 2015, Jarowski's research team combined some coordination polymers of 4-(2-pyridine)-1,2,3 triazoles with substituents on the pyridine ring and metal platinum, and studied their optical properties. The research group found that the electron-withdrawing and electron-donating effects of substituents on the pyridine ring can affect the coordination field effect, affect the activation state of Pt-Pt, and affect the luminescent properties of the complex at the supramolecular level,...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 陈云峰陈云舟胡钦铨刘艺
Owner WUHAN INSTITUTE OF TECHNOLOGY
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