Electrochemical catalysis synthesis method of 3-sulfonyl substituted oxo indoles compound

Abstract

The invention discloses an electrochemical catalysis synthesis method of a 3-sulfonyl substituted oxo indoles compound, and belongs to synthesis of compounds. The method uses a sulfoacid reagent represented by a formula (III) or sulfonyl hydrazine represented by a formula (V) or N-substituted acrylamide represented by a formula (II) as a raw material in a single-cell electrolytic tank; and in presence of an electrocatalyst, the raw material is electrolyzed in electrolyte at a certain temperature to obtain the 3-sulfonyl substituted oxo indoles compound represented by a formula (I). The method firstly adopts an operation-simple electrochemical catalysis indirect electrolysis method to synthesize the 3-sulfonyl substituted oxo indoles compound, uses the single-cell electrolytic tank and constant-current electrolysis, uses a cheap and easy-obtained graphite piece as a working electrode, largely reduces the cost, in particular, reduces heavy metal or chemical-metered oxidant, prevents generation of chemical wastes, is simpler in operation, and is more suitable for industrial production.

Description

technical field [0001] The invention relates to an electrochemical catalytic synthesis method of 3-sulfonic acid group-substituted oxindole compounds, which belongs to compound synthesis. Background technique [0002] 3-sulfonic acid substituted oxindole compounds are widely used in medicinal chemistry and synthetic chemistry, so the synthesis of these compounds has always been the focus of attention. [0003] The chemical method is a method for synthesizing 3-sulfonic acid substituted oxoindoles: [0004] 1. Wei wei et al. (Ref.Wei wei, Jiangwei wen, Daoshan Yang et al.GreenChem., 2014, 16, 2988-2991) reported a non-metal-catalyzed direct synthesis of 3-sulfonic acid substituted indoxin Indole compounds. The method is to use acetonitrile-water (1 / 2) as solvent, under the condition of 80 ℃, with stoichiometric potassium persulfate (K 2 S 2 o 8 ) is an oxidizing agent, and N-substituted methacrylamide reacts with sulfinic acid to generate 3-sulfonic acid-substituted oxoi...

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Problems solved by technology

[0005] (1) The method must use a stoichiometric amount of corrosive potassium persulfate (K 2 S 2 o 8 ) is an oxidizing agent, which is prone to danger, and produces a large amount of inorganic salt sodium sulfate (Na 2 SO 4 ), will result in the generation of chemical waste;

[0006] (2) Because this method is the source of sulfonic acid group with sodium sulfinate, certain excitant smell is arranged in the reaction process, therefore harmful to environment, human body

[0008] (1) This method must use metal Fe(NO 3 ) 3 9H 2 O acts as a catalyst, and the chemical waste produced will cause heavy metal pollution;

[0009] (2) This method also uses sodium sulfinate as the source of sulfonic acid groups, and there will be certain pungent smell in the reaction process, so it is harmful to the environment and human body

[0011] (1) This method must use stoichiometric TBHP as an oxidant, which is corrosive and dangerous

[0012] (2) This method must use pre-functionalized hydrazine sulfonate as the source of sulfonic acid groups, requiring additional raw material preparation methods

[0013] At present, the electrochemical catalytic synthesis method of 3-sulfonic acid substituted oxindole compounds under single-chamber electrolytic cell and constant current condition has not been reported in the literature at home and abroad.

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