Studies On Synthesis Of Benzyl Amine And Phenylthio-1,3,4-thiadiazole Compounds Through C-N, C-S Coupling Catalyzed By Copper

Formation of C(aryl)-N, C(aryl)-O, C(aryl)-S bonds are very important in synthetic organic chemistry from many compounds containing C(aryl)-X (N, O, S) bonds in pharmaceuticals. Because of the expensive price and violent poisonousness, limiting the palladium catalyst in the cross coupling reaction in drug synthesis of application. Therefore, copper-catalyzed Ullmann-type cross coupling reactions have become a principle method for organic synthesis in recent years. In this paper, we used copper or copper salt as catalyst, by changing the solvent and ligand to synthesis of substituted benzyl amine and substituted phenylthio-1,3,4-thiadiazole to discuss influence on this reaction. At this time, tow series of the compounds of substituted benzyl amine and substituted phenylthio-1,3,4-thiadiazole were synthesized by using this method and the synthesis methods and spectral properties were also investigated. Specific contents are as follows:1. The development of Ullmann-type reactions was reviewed, including the variety, mechanism of reaction. At the same time, the application and synthesis methods of benzyl amine and phenylthio-1,3.4-thiadiazol compounds were described in detail.2. The C-N cross coupling reaction was realized by we used substituted bromophenyl and benzylamine as raw materials, the copper(I) iodide as catalyst and the ligand of Trans-4-Hydroxy-L-proline. At the same time, a series of benzyl amine compounds were synthesized, and their structures were analysed and confirmed by IR,’H-NMR.3. The C-S cross coupling reaction was realized by we used substituted iodobenzene and substituted2-Mercapto-1,3,4-thiadiazole compounds as raw materials, while, the reaction conditions were explored and optimized. The experimental results show that in this condition including the copper (I) iodide catalyst, the ligand of2-Picolinic acid and the solvent of Dimethyl Sulfoxide, we have a good results. By using this method, a series of substituted phenylthio-1,3,4-thiadiazole were synthesized, and their structures were analysed and confirmed by IR,’H-NMR,13C-NMR, ESI-MS.