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Method for synthesizing 1-hydroxyphenothiazine compound

A technology for phenothiazines and compounds, which is applied in the field of synthesizing 1-hydroxyphenothiazine compounds, can solve the problems of high reaction temperature, complicated separation, low yield and the like, and achieves high reaction efficiency, easy availability of synthetic raw materials and wastes. less effect

Active Publication Date: 2022-03-22
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This method has some disadvantages, such as: high reaction temperature, low yield, complicated separation, corrosive and toxic gas H 2 S produces etc., thus limiting the use of these methods

Method used

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  • Method for synthesizing 1-hydroxyphenothiazine compound
  • Method for synthesizing 1-hydroxyphenothiazine compound
  • Method for synthesizing 1-hydroxyphenothiazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of o-benzoquinone:

[0031] Dissolve 1.1g of catechol in 20mL of dichloromethane to form a solution. In a 150mL three-neck flask, put 2.2g of sodium periodate and 50mL of water into it, cool and stir in an ice-water bath to dissolve, quickly add the catechol dichloromethane solution dropwise, continue stirring for 10min, extract 3×15mL of dichloromethane, combine, A solution of o-benzoquinone in dichloromethane was obtained.

[0032] Synthesis of intermediate 2-amino-2',3'-dihydroxydiphenylsulfide:

[0033] In a 250 mL three-necked flask, put 1.25 g of o-mercaptoaniline and 50 mL of dichloromethane, stir to dissolve, and add dropwise the o-benzoquinone dichloromethane solution obtained in the previous step. Half of the volume of dichloromethane was removed by rotary evaporation, and an equal volume of petroleum ether was added, and a white solid was precipitated after suction filtration. The solid was recrystallized and dried to obtain 1.67 g of a white soli...

Embodiment 2-11

[0039] Synthesize other intermediate diphenyl sulfide compounds by the same method as in Example 1, and the gained intermediate diphenyl sulfide compounds are synthesized by the same method as in Example 1 to other 1-hydroxyphenothiazine compounds, and its various reaction conditions And the reaction results are shown in Table 1.

[0040] Synthesis of various 1-hydroxyphenothiazine compounds under different conditions in table 1

[0041]

[0042]

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a synthesis method of phenothiazine compounds, in particular to a method for synthesizing 1-hydroxy phenothiazine compounds. The method comprises the following steps: taking an o-mercaptoaniline compound and a catechol compound as raw materials; the method comprises the following steps: oxidizing a catechol compound into an o-benzoquinone compound, carrying out an S-substitution reaction on the o-benzoquinone compound and an o-mercaptoaniline compound to synthesize an intermediate diphenyl sulfide compound, and carrying out catalytic oxidation dehydroxylation cyclization on the intermediate diphenyl sulfide compound to synthesize the 1-hydroxyphenothiazine compound. The method has the advantages of simple synthetic route, easily available synthetic raw materials, mild reaction conditions, high reaction efficiency, cheap catalyst, high activity, simple post-treatment and less waste, and has strong application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing phenothiazine compounds, in particular to a method for synthesizing 1-hydroxyphenothiazine compounds. Background technique [0002] Phenothiazines are a class of nitrogen- and sulfur-containing tricyclic compounds that are widely used. There are no less than a hundred kinds of phenothiazines in clinical use, and some phenothiazines have shown promising activities in anticancer, antibacterial and Alzheimer's disease treatment [Krystian Pluta, et al. European Journal of Medicinal Chemistry, 2011, 46, 3179-3189]. In recent decades, phenothiazine compounds have shown great application prospects in the fields of organic dyes, chemiluminescent materials, chemical sensors and other materials. Due to the potential biological activity and optoelectronic properties of phenene, thiazides have attracted much attention due to their special structure. There...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20
CPCC07D279/20Y02A50/30
Inventor 杨贯羽尚旭晨周寒裕豆颖超
Owner ZHENGZHOU UNIV
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