Electrochemical synthesis method of 2-substituted benzothiazole

Abstract

The invention discloses an electrochemical synthesis method of 2-substituted benzothiazole. The electrochemical synthesis method comprises the following steps that an inert electrode is adopted, 2-amino thiophenol (or 2,2'-diaminodiphenyl disulfide), iron salt, an electrolyte, an electrolytic solvent and water are added into a non-diaphragm single-chamber electrolytic tank and react under the condition with a normal temperature, a normal pressure and a constant current, and after the reaction is finished, extracting, separating and purifying are carried out to obtain the 2-substituted benzothiazole. According to the electrochemical synthesis method, cyclic ether in the reaction is used as a solvent and a substrate for the reaction; synthesis is carried out under the condition with the hightemperature, strong acid and the like in a traditional synthesis method, and the condition is relatively harsh; according to the method, the 2-substituted benzothiazole is constructed by adopting a green and environment-friendly energy source, namely electricity, as an oxidizing agent and adopting cheap iron as a catalyst under mild conditions; and the electrochemical synthesis method of the 2-substituted benzothiazole has the advantages of being simple, efficient, relatively good in yield, economic and environment-friendly, and the electrochemical synthesis method has certain industrial prospects.

Description

technical field [0001] The invention relates to the field of synthesis of 2-substituted benzothiazoles, in particular to the electrochemical synthesis of 2-substituted benzothiazoles. Background technique [0002] Substituted benzothiazoles are an important class of pharmaceutically useful heterocyclic compounds; they are present in many bioactive molecules such as the clinically used drug zopopol (for the treatment of diabetes), selective fatty acid amide hydrolase inhibitors, aldose reducing Enzyme inhibitors, antineoplastic agents, and fatty acid oxidation inhibitors. In addition, benzothiazole skeletons are often present in other molecules, such as industrial dyes, natural products, functional materials, pesticides, fluorescent indicators, and ligands for reactions. Therefore, exploring a fast and efficient method to construct benzothiazoles has aroused widespread interest of scientists. [0003] 2-substituted benzothiazoles are usually constructed by the cyclization r...

AI Technical Summary

Problems solved by technology

In the same year, the research group successfully constructed 2-substituted benzothiazole compounds through the condensation reaction of 2-aminothiophenol and ketoacid. The reaction conditions are relatively mild, but both acid and base need to be added [Wang.H. -B.; Huang.J.-M.Advanced Synthesis & Catalysis, 2016, 358, 1975-1981]

To the best of our knowledge, the direct construction of 2-substituted benzothiazoles via the reaction of 2-aminothiophenol (or 2,2'-diaminodiphenyldisulfide) with cyclic ethers has not been reported

Images