Background: Sulfur-containing organic compounds are an important group of organic compounds that play an important role in natural compounds such as coenzymes and peptides. These compounds have been of great interest in the development of drugs and in industry. Although the formation of carbon-sulfur bond has been studied a lot, but the formation of this bond brings disadvantages such as the use of expensive raw materials or the poisoning of metal catalysts by sulfur-containing compounds. In this research, a new method for the synthesis of S-aryl-3-(alkylthio)propanethioates, which has two carbon-sulfur bonds in its structure, is presented. Of the advantages of this method include the high speed of the reaction, the ease of the method and the good efficiency of the products.
Aim: The aim of this study is the synthesis of S-aryl-3-(alkylthio)propanethioates from thiols in the presence of stable and resistant triphenylphosphine catalyst.
Methodology: In this study, the reaction of aromatic and aliphatic thiols with maleic anhydride in the presence of triphenylphosphine catalyst for the synthesis of S-aryl-3-(alkylthio)propanethioates has been investigated. First, the reaction conditions were optimized by screening the solvent and using different amounts of raw materials and catalysts at different temperatures. The obtained optimal conditions were used to prepare other derivatives of S-aryl-3-(alkylthio)propanethioate.
Findings: Achieving a new method for the synthesis of S-aryl-3 (alkylthio)propanethioates in acetonitrile solvent in the vicinity of triphenylphosphine catalyst
Conclusions: In this research, an easy and efficient method for the synthesis of S-aryl-3-(alkylthio)propanethioates using cheap and available materials such as thiols, maleic anhydride and triphenylphosphine has been presented. In this method, two carbon-sulfur bonds are formed. The first bond is formed by aromatic thiol with nucleophilic attack on maleic anhydride and the second bond is formed