24192-81-2Relevant academic research and scientific papers
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.
Hypervalent iodine promoted: Ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates
Saha, Moumita,Das, Asish R.
supporting information, p. 941 - 955 (2020/02/15)
The mild and efficient palladium-catalyzed ortho C(sp2)-H diversification of (NH)-free 2-substituted benzimidazole, quinazoline, and imidazopyridine is reported using hypervalent iodine as the key reagent. Acetoxy, aryl, iodide and nitro functi
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.
N-Heterocycle-Stabilized Iodanes: From Structure to Reactivity
Boelke, Andreas,Lork, Enno,Nachtsheim, Boris J.
, p. 18653 - 18657 (2018/11/23)
Pseudocyclic aryl-λ3-iodanes are superior reagents for a variety of oxidative transformations due to a well-balanced relation between stability, solubility and reactivity. Their properties are substantially influenced by a dative interaction between a Lewis base, in general the oxygen atom of a carboxylic acid or an amide, and the central hypervalent iodine atom. This work presents the first systematic investigation of pseudocyclic N-heterocycle-stabilized iodanes (NHIs). The synthesis of these throughout shelf-stable solids is robust and can be achieved on a large scale. Their reactivity is highly tunable, depending on the stabilizing heterocycle. Solid state structures of selected derivatives are reported and their reactivity in a model oxygen transfer reaction is compared. Further derivatization reactions to N-heterocycle-stabilized pseudocyclic diaryliodonium salts and cyclic iodoso species are presented as well.
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.
IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides
Moorthy, Jarugu Narasimha,Neogi, Ishita
, p. 3868 - 3871 (2011/08/06)
A variety of primary alcohols are shown to be converted to the corresponding benzimidazoles in one pot by employing IBX and o-phenylenediamine in DMSO at room temperature. o-Iodobenzoic acid is the end product of IBX, which is employed in 1.0 equiv. Arylmethyl bromides are also shown to be converted likewise to benzimidazoles in moderate yields in one pot, albeit at slightly elevated temperatures.
Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators
Charton, Julie,Girault-Mizzi, Sophie,Debreu-Fontaine, Marie-Ange,Foufelle, Fabienne,Hainault, Isabelle,Bizot-Espiard, Jean-Guy,Caignard, Daniel-Henri,Sergheraert, Christian
, p. 4490 - 4518 (2007/10/03)
Design, synthesis and structure-activity relationships of benzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure-activity relationships are being described.
