4858-36-0Relevant articles and documents
Metal-free and green synthesis of a series of new bis(2-alkylsulfanyl-[1,3,4]thiadiazolyl)-5,5′-disulfides and 2,2′-Dibenzothiazyl disulfide via oxidative self-coupling using hydrogen peroxide
Ching Juan, Joon,Ghaffari Khaligh, Nader,Heidelberg, Thorsten,Ling Ong, Chiu
, (2021/12/29)
Many disulfide and 1,3,4-thiadiazole-1,2-dithiol compounds have been extensively investigated in the pharmaceutical industry due to their unique biological properties. A series of new bis(2-alkylsulfanyl-[1,3,4]thiadiazolyl)-5,5′-disulfide derivatives containing two 1,3,4-thiadiazole rings linked by S[sbnd]S bond spacer were synthesized via the oxidative self-coupling of 5-alkylsulfanyl-[1,3,4]thiadiazole-2-thiol using hydrogen peroxide and ethanol as green oxidant and solvent, respectively. The excellent yields of 93–97% with 100% conversion were achieved with a simple one-pot synthesis. There is no over-oxidation of 5-alkylsulfanyl-[1,3,4]thiadiazole-2-thiol and 2-mercaptobenzothiadiazole that leads to the formation of by-products such as thiosulfinate, thiosulfonate, and sulfonic acid. In this process, a straightforward, short reaction time, metal-free, reusable solvent, and mild reaction conditions are applied to produce bis(2-alkylsulfanyl-[1,3,4]thiadiazolyl)-5,5′-disulfides and 2,2′-dibenzothiazyl disulfide. Therefore, the oxidative self-coupling is potential for other disulfide compounds.
Kinetic investigation of the alkylation of salts of 2,5-dimercapto-1,3,4-thiadiazole
Kuodis,Rutavichyus,Valiulene
, p. 857 - 861 (2007/10/03)
A kinetic investigation has been carried out, using electronic absorption spectra, of the alkylation with benzyl chloride of the dihydrazine, monohydrazine, and the disodium salts of 2,5-dimercapto-1,3,4-thiadiazole, and also of the hydrazine and sodium salts of 5-benzylthio-2-mercapto-1,3,4-thiadiazole. The rates orders and constants were established for the benzylation reaction and it was noted that the reaction rate depends on the cation of these salts and the degree of substitution of the 2,5-dimercapto-1,3,4-thiadiazole.