98948-98-2Relevant academic research and scientific papers
A rapid, mild, and efficient method for C-5 iodination/thiocyanation of 2-aminothiazoles
Hebade, Madhav J.,Kamble, Rahul D.,Hese, Shrikant V.,Mogle, Pratima P.,Ambhore, Ajay N.,Kadam, Shuddhodan N.,Dawane, Bhaskar S.
, p. 1155 - 1159 (2016)
An efficient, green, rapid multitasking protocol for the selective C-5 substitution of 2-aminothiazole using iodic acid and aqueous PEG-400 was developed. The method found suitable for C-5 substitution i.e. iodination and thiocyanation of 2-amino thiazole
ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light
Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi,Sarvestani, Abdollah Masoudi
, p. 1401 - 1407 (2020/03/26)
An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.
Visible light thiocyanation of: N -bearing aromatic and heteroaromatic compounds using Ag/TiO2 nanotube photocatalyst
Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi
supporting information, p. 19237 - 19244 (2018/11/27)
In this study, Ag/TiO2 nanotubes (Ag/TNT) were synthesized via simple hydrothermal process, and this photocatalyst was successfully exploited in thiocyanation reactions at room temperature under visible light irradiation. Four classes of important heterocyclic compounds including indole, aniline, pyrrole and 2-amino thiazole derivatives via Ag/TNT treated with ammonium thiocyanate formed the corresponding thiocyano compounds in moderate to excellent yields. Plasmonic property and catalytic performance of Ag nanoparticles (which mainly deposited on the surface of TNT) in absorbing species containing sulfur atoms were key components for the reactions to proceed. This potent, simple and versatile protocol reported for the first time afforded thiocyanation reactions of aniline, pyrrole and 2-amino thiazole derivatives under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low-cost and environmentally friendly terminal oxidant.
Metal-Free One-Pot Chemoselective Thiocyanation of Imidazothiazoles and 2-Aminothiazoles with in situ Generated N-Thiocyanatosuccinimide
Kadam, Shuddhodan N.,Ambhore, Ajay N.,Hebade, Madhav J.,Kamble, Rahul D.,Hese, Shrikant V.,Gaikwad, Milind V.,Gavhane, Priya D.,Dawane, Bhaskar S.
, p. 1902 - 1908 (2018/08/28)
A chemoselective thiocyanation of imidazothiazoles and 2-aminothiazoles with use of in situ generated N-thiocyanatosuccinimide (NTS) at room temperature is described. The protocol offers mild reaction conditions and high chemoselectivity for electrophilic substitution in imidazothiazoles over nucleophilic substitution. This method provides metal-free and easy conversion of imidazothiazoles and 2-aminothiazoles into their corresponding C-3 and C-5 thiocyanates, respectively, in good to excellent yield. The present protocol also offers the effective thiocyanation of bifunctional imidazothiazoles containing aliphatic -OH and C(sp 2)-H bond functionalities.
Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts
Chen, Binhui,Guo, Shanshan,Guo, Xiao,Zhang, Guolin,Yu, Yongping
supporting information, p. 4698 - 4701 (2015/10/12)
A highly selective construction of 4-substituted 2-aminothiazoles and 4-substituted 5-thiocyano-2-aminothiazoles, respectively, catalyzed by palladium(II) acetate and promoted by iron(III) bromide from vinyl azides and potassium thiocyanate has been developed. Use of readily available starting materials, high selectivity, as well as mild reaction conditions make this practical method particularly attractive.
