13604-44-9Relevant academic research and scientific papers
Copper-Catalyzed Double Thiolation to Access Sulfur-Bridged Imidazopyridines with Isothiocyanate
Tian, Lu-Lu,Lu, Shuai,Zhang, Zhe-Hua,Huang, En-Ling,Yan, Hua-Ting,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 5213 - 5221 (2019/05/10)
A copper(I)-catalyzed sulfur-bridged dimerization of imidazopyridines has been developed using isothiocyanate as the sulfur source. This method enables a switchable synthesis of bis(imidazo[1,2-a]pyridin-3-yl)sulfanes or bis(2-(imidazo[1,2-a]pyridin-2-yl)phenyl)sulfanes in the presence of 4-dimethylaminopyridine (DMAP) or K2CO3 when different imidazopyridines were employed. Under optimized conditions, a variety of sulfur-bridged imidazopyridines were obtained in good yields. Moreover, thiourea was proved to be the key intermediate under catalytic system A.
Copper-catalyzed C-H bond direct chalcogenation of aromatic compounds leading to diaryl sulfides, selenides, and diselenides by using elemental sulfur and selenium as chalcogen sources under oxidative conditions
Shibahara, Fumitoshi,Kanai, Takafumi,Yamaguchi, Eiji,Kamei, Akika,Yamauchi, Takayuki,Murai, Toshiaki
, p. 237 - 244 (2014/01/06)
The reactions of aromatic compounds and elemental chalcogens catalyzed by a copper salt with molecular oxygen as an oxidant were carried out. The reaction of 3-substituted imidazo[1,5-a]pyridines and elemental sulfur in the presence of CuTC (copper(I) thiophenecarboxylate) gave the corresponding bisimidazopyridyl sulfides in good to quantitative yields. The reaction proceeded even under aerobic oxidation conditions. The use of a polar solvent was crucial for the reaction, and DMSO (dimethyl sulfoxide) in particular stimulated the reaction. The reaction could be applied to common aromatic compounds, such as N-methyl indole and dialkyl anilines. The reaction of indole proceeded at the nucleophilic C3 position rather than at the acidic C2 position. In addition, the reaction of dialkyl anilines proceeded with an ortho, para orientation. The reactions of imidazopyridines and elemental selenium under similar conditions gave the corresponding bisimidazopyridyl diselenides along with bisimidazopyridyl monoselenides. The resulting diselenides were readily converted to the corresponding monoselenides with unreacted imidazopyridines under the same conditions. The reaction could be applied to the copolymerization of bifunctional bisimidazopyridines and elemental sulfur to give oligomeric copolymers in quantitative yield. Copyright
Utilisations synthetiques d'une electrode soluble au soufre. IV. Creation de l'enchainement C-S-C a partir d'hydrocarbures aromatiques, d'heterocycles et d'amines aromatiques
Do, Quang Tho,Elothmani, Driss,Simonet, Jacques,Guillanton, Georges Le
, p. 789 - 793 (2007/10/02)
Use of a sacrificial sulfur electrode in electroorganic chemistry.IV.Formation of the C-S-C bond from aromatic hydrocarbons, heterocycles and aromatic amines.The electrophile S2+ was prepared in organic media by oxidation of a carbon-sulfur electrode.This species can react with aromatic hydrocarbons, heterocycles and aromatic amines to produce organic monosulfides. carbon-sulfur electrode / sacrificial electrode / sulfur cation / organic sulfide / electrophilic substitution
PHOTOCHEMICAL SUBSTITUTION OF HALOGEN AND SO2X GROUPS BY THIOUREA AND THIOSEMICARBAZIDE. PHOTOSYNTHESIS OF AROMATIC DISULFIDES
Frolov, A. N.,Klokova, E. M.,El'tsov, A. V.
, p. 1926 - 1935 (2007/10/02)
During UV irradiation in the presence of thiourea (or thiosemicarbazide) the para- and ortho-halogen and sulfonyl derivatives of the benzene, naphthalene, and heterocyclic series with donating substituents in the ring are converted into arylisothiuronium salts.Thermal hydrolysis and oxidation of these salts lead to the formation of the respective diaryl disulfides in the case of the para isomers and thiazoles for the ortho isomers.
