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Method for generating 2-aminophenoloxazine-3-ketone compound by catalyzing oxidation of molecular oxygen in water phase

A technology of aminophenol oxazine and ketone compounds, applied in organic chemistry, etc., can solve the problems of low yield of target products in cross-coupling reactions, difficulty in avoiding salty wastewater, difficult post-treatment, etc., and achieve strong industrial application prospects , environmental friendliness, catalyst simple effect

Active Publication Date: 2020-05-29
PHARMARON BEIJING
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The catalysts used in these methods are often complex and costly, and some use organic solvents to cause post-treatment difficulties, and it is difficult to avoid the generation of saline wastewater. The important thing is that the yield of the target product of the cross-coupling reaction is low, which limits these methods. Method usage

Method used

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  • Method for generating 2-aminophenoloxazine-3-ketone compound by catalyzing oxidation of molecular oxygen in water phase
  • Method for generating 2-aminophenoloxazine-3-ketone compound by catalyzing oxidation of molecular oxygen in water phase
  • Method for generating 2-aminophenoloxazine-3-ketone compound by catalyzing oxidation of molecular oxygen in water phase

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Synthesis of 2-aminophenoxazin-3-one:

[0030] In a 150mL reactor, put 2.18g o-aminophenol, 218mg gallic acid, 2mg cobalt chloride, 13mg manganese sulfate, 138mg K 2 CO 3 and 80mL of water; heated to 15°C with stirring, introduced oxygen, kept the pressure in the reactor at 1.0MPa, stopped the reaction after 18 hours of reaction, cooled to room temperature, extracted with 3×15mL ethyl acetate, combined the ethyl acetate layers, Ethyl acetate was removed by rotary evaporation, and the remaining solid was recrystallized with isopropanol, suction filtered, and dried to obtain 2.04 g of a black solid. The product was passed through NMR (see attached figure 1 and 2 ), MS and other methods determine that the structure is 2-aminophenol oxazin-3-one, the yield is 94%, and the purity of the product analyzed by liquid chromatography is 97%.

Embodiment 2

[0032] Synthesis of 4-chloro-2-aminophenoxazin-3-one:

[0033] In a 150mL reactor, put 1.09g 2-aminophenol, 1.44g 4-chloro-2-aminophenol, 14mg gallic acid, 72mg copper chloride, 0.67g KOH and 65mL water; Air, keep the pressure in the reactor at 0.1MPa, stop the reaction after 4 hours of reaction, cool to room temperature, extract with 3×15mL ethyl acetate, combine the ethyl acetate layer, rotary evaporate to remove ethyl acetate, and reweight the remaining solid with isopropanol Crystallization, suction filtration, oven dry, obtain black solid 2.2g, product is through NMR (see attached image 3 and 4 ), MS and other methods determined that the structure was 7-chloro-2-aminophenoxazin-3-one, the yield was 87%, and the purity of the product analyzed by liquid chromatography was 97%.

[0034] Other 2-aminophenoxazin-3-one compounds were synthesized in the same manner as in Example 1, and their various reaction conditions and reaction results are shown in Table 1.

[0035] Tabl...

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Abstract

The invention provides a method for generating a 2-aminophenoloxazine-3-ketone compound by catalyzing oxidation of molecular oxygen in a water phase. According to the method, gallic acid is used as acatalyst, metal salts are used as a co-catalyst, and an o-aminophenol compound carries out reactions in a water phase in an oxygen or air environment in the presence of an alkali to generate the 2-aminophenoloxazine-3-ketone compound. The reaction is carried out in a water phase, and other organic solvents do not need to be added. The catalyst is simple, high in catalytic activity and high in reaction efficiency; and the method is simple in synthesis process, less in waste and environment-friendly, and has a wide industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic heterocyclic compounds, in particular to a method for catalyzing the oxidation of molecular oxygen in an aqueous phase to generate 2-aminophenoloxazin-3-one compounds. Background technique [0002] Phenoxazinone alkaloids are widely distributed in nature and are considered to be a unique class of natural tricyclic heterocyclic compounds. Studies have found that phenoxazinone compounds have a wide range of medicinal properties, including anti-tumor, anti-viral, anti-inflammatory, anti-bacterial, anti-Alzheimer's disease and so on. For example, Actinomycin D has been clinically used to treat various types of cancer. Therefore, phenoxazinone is often used as the core structure of new drugs in medicinal chemistry research. Phenoxazinones are also key structures of natural dyes and fluorescent probes. Among them, 2-aminophenoxazin-3-one compounds have attracted much attention. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38
CPCC07D265/38
Inventor 杨贯羽李文豪段文雪
Owner PHARMARON BEIJING
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