17467-15-1Relevant articles and documents
Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation
Yu, Wentao,Huang, Yubing,Li, Jianxiao,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
, p. 9334 - 9343 (2018/07/30)
A copper-catalyzed aerobic oxidative annulation reaction of 2-aminopyridine/amidine with isothiocyanate has been reported. This strategy involving C-N/N-S bond formations provides various 5-amino/imino-substituted 1,2,4-thiadiazole derivatives under a Cu/O2 catalytic system. This method has demonstrated high reactivity, mild reaction conditions, and a broad substrate scope. Furthermore, the synthetic utilities of the approach are demonstrated by further modifications.
Facile synthesis of substituted 5-amino- And 3-amino-1,2,4-thiadiazoles from a common precursor
Wehn, Paul M.,Harrington, Paul E.,Eksterowicz, John E.
scheme or table, p. 5666 - 5669 (2010/03/01)
[Chemical Equation Presented] A novel approach to the synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles beginning from a common precursor has been achieved. Derivatization by palladium-catalyzed Suzuki-Miyaura coupling enables the rapid pre
Photoinduced molecular rearrangements. The photochemistry of 1,2,4-oxadiazoles in the presence of sulphur nucleophiles. Synthesis of 1,2,4-thiadiazoles
Vivona, Nicolo,Buscemi, Silvestre,Asta, Stefano,Caronna, Tullio
, p. 12629 - 12636 (2007/10/03)
The photochemistry of some 1,2,4-oxadiazoles in the presence of sulphur nucleophiles has been investigated. Irradiation of the 5-amino-3-phenyl- and 3,5-diphenyl-1,2,4-oxadiazole at λ = 254 nm in methanol in the presence of sodium hydrogen sulphide or thiols gave a photo-induced redox reaction at the ring O-N bond, leading to the corresponding N-substituted benzamidines. By contrast, irradiation of the 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioureas or thiocarbamates, essentially gave 3-phenyl-5-substituted 1,2,4-thiadiazoles, which presume an N-S bond formation between the ring-photolytic species and the sulphur nucleophile. In turn, irradiation of the same 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioamides again afforded the redox reaction; in addition, amounts of 3-phenyl-5-substituted-1,2,4-thiadiazoles were also formed. Some mechanistic considerations are reported and synthetic methodologies leading to 1,2,4-thiadiazoles are emphasized.