82725-45-9Relevant academic research and scientific papers
Synthesis of Benzo[4,5]thiazolo[2,3-c][1,2,4]triazole Derivatives via C-H Bond Functionalization of Disulfide Intermediates
Ardón-Mu?oz, Luis G.,Bolliger, Jeanne L.
, (2022/03/01)
Many nitrogen-and sulfur-containing heterocyclic compounds exhibit biological activity. Among these heterocycles are benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles for which two main synthetic approaches exist. Here we report a new synthetic protocol that allows the preparation of these tricyclic compounds via the oxidation of a mercaptophenyl moiety to its corresponding disulfide. Subsequent C-H bond functionalization is thought to enable an intramolecular ring closure, thus forming the desired benzo[4,5]thiazolo[2,3-c][1,2,4]triazole. This method combines a high functional group tolerance with short reaction times and good to excellent yields.
Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
supporting information, p. 7851 - 7856 (2019/10/11)
A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols with Aryl and Heteroaryl Iodides via Thiyl Radicals
Oderinde, Martins S.,Frenette, Mathieu,Robbins, Daniel W.,Aquila, Brian,Johannes, Jeffrey W.
supporting information, p. 1760 - 1763 (2016/03/01)
Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C-S cross-coupling was achieved versus competitive C-O and C-N cross-couplings. This C-S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular oxygen. Mechanistic investigations indicated that the reaction proceeded through transient Ni(I)-species and thiyl radicals. Distinct from nickel-catalyzed cross-coupling reactions involving carbon-centered radicals, control experiments and spectroscopic studies suggest that this C-S cross-coupling reaction does not involve a Ni(0)-species.
