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A kind of preparation method of tetrahydrophenazine derivative

A technology of tetrahydrophenazine and derivatives, which is applied in the field of preparation of tetrahydrophenazine derivatives, can solve the problems of high price of phenazine compounds, difficult commercialization, expensive reagents, etc., and achieves low catalyst usage and raw materials. Non-toxic, good compatibility

Active Publication Date: 2022-04-22
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Traditional methods of synthesizing phenazines require expensive reagents and produce useless by-products that make commercialization difficult, resulting in high prices for phenazine compounds

Method used

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  • A kind of preparation method of tetrahydrophenazine derivative
  • A kind of preparation method of tetrahydrophenazine derivative
  • A kind of preparation method of tetrahydrophenazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] Add 0.25 mmol 2-nitroaniline, 0.35 mmol o-diphenol, 0.0075 mmol palladium carbon, 0.05 mmol potassium carbonate, 1.5 ml p-xylene to a schlenk tube, at 120 °C, H 2 Under conditions (the hydrogen pressure used is one atmospheric pressure) after stirring and reacting for 12 hours, stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether: ethyl acetate mixed solvent is 15:1, and the yield is 74%.

[0045] of the resulting product 1 H-NMR spectrum and 13 The C-NMR spectra are as follows figure 1 and figure 2 As shown, the structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3): δ7.97(dd, J=6.4, 3.2Hz, 2H), 7.66(dd, J=6.0, 3.2Hz, 2H), 3.17(s, 4H), 2.09-2.01(m, 4H). 13 C NMR (101MHz, CDCl 3 ): δ154.14, 141.21, 128.91, 128.34, 33.21, 22.80. IR(KB...

Embodiment 2

[0047]

[0048] Add 0.25 mmol 4-methoxy-2-nitroaniline, 0.35 mmol o-diphenol, 0.0075 mmol palladium carbon, 0.1 mmol potassium carbonate, 1.5 ml p-xylene to a schlenk tube at 120 °C, H 2 Under conditions (the hydrogen pressure used is one atmospheric pressure) after stirring and reacting for 12 hours, stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether:ethyl acetate mixed solvent is 8:1, and the yield is 85%.

[0049] of the resulting product 1 H-NMR spectrum and 13 The C-NMR spectra are as follows image 3 and Figure 4 As shown, the structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.72(d, J=9.1Hz, 1H), 7.19(dd, J=9.1, 2.7Hz, 1H), 7.14(d, J=2.7Hz, 1H), 3.81(s, 3H), 3.00 (d, J=4.2Hz, 4H), 1.90 (dd, J=6.5, 3.0Hz, 4H). 13 C NMR (101MHz, CDCl ...

Embodiment 3

[0051]

[0052] Add 0.25 mmol 5-(4-methylpiperazine)-2-nitroaniline, 0.5 mmol catechol, 0.015 mmol palladium hydroxide on carbon, 0.05 mmol cesium carbonate, 1.5 ml toluene to a schlenk tube, at 110°C, H 2 After stirring and reacting for 16 hours under conditions (the hydrogen pressure used is one atmospheric pressure), stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether:ethyl acetate mixed solvent is 6:1, and the yield is 80%.

[0053] of the resulting product 1 H-NMR spectrum and 13 The C-NMR spectra are as follows Figure 5 and Image 6 As shown, the structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.73(d, J=9.3Hz, 1H), 7.35(dd, J=9.3, 2.4Hz, 1H), 7.12(d, J=2.4Hz, 1H), 3.35-3.27(m, 4H) , 3.01 (d, J=2.0Hz, 4H), 2.57-2.49 (m, 4H), 2.28 (s, ...

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Abstract

The preparation method of the present invention comprises the following steps: in a reactor, add nitroamine compounds, diphenol compounds, metal catalysts, additives, reducing agents and solvents, and stir for reaction to obtain tetrahydrophenazine derivatives; The structure of nitroamine compound is as shown in general formula (1), and the structure of described diphenol compound is as shown in general formula (2); Wherein, R 1 independently selected from methyl, methoxy, amino, piperidinyl or trifluoromethyl; R 2 are independently selected from methyl groups or ester groups; n and m represent integers of 0-4 respectively. The present invention uses stable and readily available nitroaniline compounds and biomass-derived diphenol compounds as raw materials to synthesize tetrahydrophenazine derivatives in one step, and has the advantages of simple synthesis steps, non-toxic, cheap and readily available raw materials, and low catalyst usage The synthetic method has the advantages of good functional group compatibility and high atom economy, and has the potential to prepare tetrahydrophenazine derivatives in one step on a large scale.

Description

technical field [0001] The invention relates to a preparation method of tetrahydrophenazine derivatives, belonging to the technical field of organic synthesis. Background technique [0002] As an important branch of quinoxaline derivatives, tetrahydrophenazine exhibits a wide range of physiological and pharmaceutical activities. Its earliest application was as a dye, and then it was found that they have biological activity and can be used as a fungicide. In recent years, relevant studies have found that tetrahydrophenazine derivatives are mainly used as important module molecules, which are used in fluorescent biomarkers, dyes, organic semiconductors, solar cells and other fields. (Eur. J. Med. Chem. 2017, 125, 710-721; ACS Omega 2017, 2, 2694-2705; Dalton Trans. 2015, 44, 3467-3485). [0003] The traditional method for preparing tetrahydrophenazine is to synthesize o-phenylenediamine and phenols, or 2-nitrophenylenediamine and its substitutes as starting materials. (1) Us...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/46
CPCC07D241/46
Inventor 谢锋张珉李亦彪马炜林何建文高淑雯
Owner WUYI UNIV
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