24192-81-2Relevant articles and documents
Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts
Vlasenko, Yulia A.,Postnikov, Pavel S.,Trusova, Marina E.,Shafir, Alexandr,Zhdankin, Viktor V.,Yoshimura, Akira,Yusubov, Mekhman S.
, p. 12056 - 12070 (2018)
Pseudocyclic 2-benzimidazolyl-substituted diaryliodonium salts were obtained by the reaction of the corresponding [hydroxy(tosyloxy)iodo]arenes with arenes in the presence of trifluoromethanesulfonic acid. X-ray structural analysis of these iodonium salts confirmed their pseudocyclic structure with a short (2.57-2.58 ?) noncovalent I···N interaction. Treatment of 2-benzimidazolyl-substituted diaryliodonium triflates with a base afforded novel five-membered iodine-nitrogen heterocycles.
Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation
Boelke, Andreas,Vlasenko, Yulia A.,Yusubov, Mekhman S.,Nachtsheim, Boris J.,Postnikov, Pavel S.
supporting information, p. 2311 - 2318 (2019/10/16)
The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.
Benzoyl methyl phosphates as efficient reagents in the one-pot tandem approach for the synthesis of 2-phenylbenzimidazoles in water
Hikawa, Hidemasa,Imani, Maki,Suzuki, Hideharu,Yokoyama, Yuusaku,Azumaya, Isao
, p. 3768 - 3773 (2014/01/06)
A novel and efficient method for the environmentally benign, catalyst- and auxiliary-free synthesis of 2-phenylbenzimidazoles in water is developed. Benzoyl methyl phosphates play important roles as biomimetic acylating agents for the one-pot tandem approach without additional catalysts.