Efficient preparation method of polysubstitution phenazine derivative and oxide thereof

A technology of derivatives and oxides, which is applied in the field of efficient preparation of multi-substituted phenazine derivatives and their oxides, can solve problems such as poor preparation and complexity, and achieve simple and easy-to-operate synthesis process, easy-to-use products, and high-efficiency preparation methods. Scientific and reasonable effect

Active Publication Date: 2018-04-17
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the substrates of this type of reaction are complex and difficult to prepare.

Method used

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  • Efficient preparation method of polysubstitution phenazine derivative and oxide thereof
  • Efficient preparation method of polysubstitution phenazine derivative and oxide thereof
  • Efficient preparation method of polysubstitution phenazine derivative and oxide thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of 3-methylphenazine-5-oxide

[0044]

[0045] Method 1: Weigh di-p-tolyliodonium trifluoromethanesulfonate (1mmol, 458mg), benzofurazan (1mmol, 120mg), cuprous bromide (0.1mmol, 14.2mg) in a 25mL sealed tube, Add magneton, replace with high-purity nitrogen three times, add 5mL dichloroethane to the sealed tube under nitrogen protection, tighten the sealed tube, move it into an oil bath at 70°C and stir, and react for 12 hours. The reaction was followed by TLC detection, and after the reaction was completed, the sealed tube was cooled to room temperature. Add 5 mL of distilled water to the system to quench the reaction, stir; extract 3 times with 5 mL of dichloromethane, combine the organic phases, add magnesium sulfate to dry, and remove the solvent with a rotary evaporator to obtain a crude product; the crude product is loaded on silica gel and eluted The solvent was purified by column chromatography using petroleum ether:ethyl acetate=10:1 i...

Embodiment 2

[0058] Example 2 Preparation of 1-chlorophenazine-5-oxide

[0059]

[0060] Method: Weigh di-2-chlorophenyliodonium trifluoromethanesulfonate (1mmol, 458mg), benzofurazan (1mmol, 120mg), cuprous bromide (0.06mmol, 8.52mg) in a 25mL sealed tube Add magnetons, replace with high-purity nitrogen for three times, add 5mL of dichloroethane to the sealed tube under nitrogen protection, tighten the sealed tube, move it into an oil bath at 70°C and stir, and react for 15 hours. The reaction was followed by TLC detection, and after the reaction was completed, the sealed tube was cooled to room temperature. Add 5 mL of distilled water to the system to quench the reaction, stir; extract 3 times with 5 mL of dichloromethane. The organic phases were combined, dried by adding magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain a crude product; the crude product was loaded on silica gel, and the eluent was purified by column chromatography with a volume ratio o...

Embodiment 3

[0068] Example 3 Preparation of 2-methoxy-7-methylphenazine-5-oxide

[0069]

[0070] Method: Weigh di-p-tolyliodonium trifluoromethanesulfonate (1mmol, 458mg), 5-methoxybenzofurazan (1mmol, 150mg), cuprous bromide (0.15mmol, 21.3mg) in 25mL Add magnetons to the sealed tube, replace it with high-purity nitrogen three times, add 7mL dichloroethane to the sealed tube under nitrogen protection, tighten the sealed tube, move it into an oil bath at 80°C and stir, and react for 20 hours . The reaction was followed by TLC detection, and after the reaction was completed, the sealed tube was cooled to room temperature. Add 5 mL of distilled water to the system to quench the reaction, stir; extract 3 times with 5 mL of dichloromethane. The organic phases were combined, dried by adding magnesium sulfate, and the solvent was removed by a rotary evaporator to obtain a crude product; the crude product was loaded on silica gel, and the eluent was purified by column chromatography with a...

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Abstract

The invention belongs to the technical field of chemical medicine preparation, and relates to an efficient preparation method of a polysubstitution phenazine derivative and oxide thereof. The preparation method comprises the steps that diaryl hypervalent iodized salt, benzo furazan and a copper-based catalyst are added into a reactor, after nitrogen is pumped and changed for three times, a solventis added, and a heating reaction is conducted after materials are added; after the reaction is completed, the mixture is cooled to be the room temperature, and phenazine oxide pure product is prepared after post-treatment, separation and purification are conducted on the mixture; and the phenazine oxide product can be further reduced, and the phenazine derivative is prepared after post-treatment,separation and purification are conducted on the phenazune oxide product. The preparation method of the polysubstitution phenazine derivative and the oxide thereof, provieded by the invention is scientific and reasonable, the asymmetrical polysubstitution phenazine derivative which is difficult to synthesize by using other methods can be synthesized and obtained, the preparation method is simple,the productive rate is high, and the product is easy to purify.

Description

technical field [0001] The invention belongs to the technical field of chemical medicine preparation, and in particular relates to an efficient preparation method of multi-substituted phenazine derivatives and oxides thereof. Background technique [0002] Phenazine oxide is phenazine-5-oxide, also known as diazenthracene 5-oxyphenazine, or xanthone. Ethanol and ether are easily soluble in benzene but hardly soluble in water, and can form salt with hydrochloric acid under certain conditions. Phenazine-5-oxide derivatives are compounds of great research and application value, which are contained in a variety of pesticides, dyes, optoelectronic materials, natural products and metabolites. [0003] Phenazine is a colorless or light yellow needle-like crystal, almost insoluble in water, slightly soluble in ethanol, ether and benzene, soluble in inorganic acids to form a yellow to red solution. Phenazine derivatives widely exist in natural products and are widely used in various...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/52C07D241/46
CPCC07D241/46C07D241/52
Inventor 陈超盛金宇何如
Owner TSINGHUA UNIV
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