2196-13-6Relevant articles and documents
Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
supporting information, p. 3398 - 3402 (2021/06/25)
Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
, p. 170 - 175 (2018/01/17)
A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
New promising methods of synthesis of pyridinecarbothioamides
Khromova, N. Yu.,Malekin,Kutkin,Kondrat'Ev
, p. 2295 - 2298 (2015/11/24)
New methods of synthesis of pyridinecarbothioamides from the corresponding cyanopyridines with the use of phosphorus pentasulfide as a thiontion agent were developed. The first method was based on the reaction of cyanopyridine with phosphorus pentasulfide in alcoholic ammonium solution followed by hydrolysis. The method provided the corresponding thioamides in 60-90% yield. The second procedure included the reaction of phosphorus pentasulfide with 4-cyanopyridine in aqueous ammonia solution, which led to the formation of pyridine-4-carbothioamides in quantitative yield.