69180-50-3Relevant academic research and scientific papers
Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts
Antonkin, Nikita S.,Vlasenko, Yulia A.,Yoshimura, Akira,Smirnov, Vladimir I.,Borodina, Tatyana N.,Zhdankin, Viktor V.,Yusubov, Mekhman S.,Shafir, Alexandr,Postnikov, Pavel S.
, p. 7163 - 7178 (2021/05/29)
A novel approach to the preparation of imidazole-substituted cyclic iodonium salts has been developed via the oxidative cyclization of 1-phenyl-5-iodoimidazole using a cheap and available Oxone/H2SO4 oxidative system. The structure of the new polycyclic heteroarenes has been confirmed by single-crystal X-ray diffractometry, revealing the characteristic structure features for cyclic iodonium salts. The newly produced imidazole-flanked cyclic iodonium compounds were found to readily engage in a heterocyclization reaction with elemental sulfur, affording benzo[5,1-b]imidazothiazoles in good yields.
Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents
Sousa E Silva, Felipe Cesar,Van, Nguyen T.,Wengryniuk, Sarah E.
supporting information, p. 64 - 69 (2020/01/22)
α-Arylation of α,β-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of α-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H α-arylation would offer an atom- and step-economical alternative, but such reports are scarce. Herein we report the metal-free direct C-H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of in situ-generated β-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O2CCF3)2 reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a β-pyridinium moiety is critical for the desired C-C bond formation.
Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information, p. 1919 - 1925 (2018/03/28)
A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles
Wu, Yichen,Izquierdo, Susana,Vidossich, Pietro,Lledós, Agustí,Shafir, Alexandr
supporting information, p. 7152 - 7156 (2016/07/06)
The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.
An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion
Haskali, Mohammad B.,Telu, Sanjay,Lee, Yong-Sok,Morse, Cheryl L.,Lu, Shuiyu,Pike, Victor W.
, p. 297 - 302 (2016/01/15)
Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.
Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents
Buendia, Julien,Darses, Benjamin,Dauban, Philippe
supporting information, p. 5697 - 5701 (2015/06/16)
A new tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations. I(003) is a double agent: A tandem C-N and C-C bond-forming reaction has been achieved through RhII/Pd0 catalysis. The sequence first involves an iodine(III) oxidant, then the in situ generated iodine(I) by-product is used as a coupling partner. The overall process affords complex building blocks with high yields, and demonstrates the synthetic value of iodoarenes produced in trivalent iodine reagent mediated oxidations.
Rapid and efficient radiosyntheses of meta-substituted [ 18F]fluoroarenes from [18F]fluoride ion and diaryliodonium tosylates within a microreactor
Chun, Joong-Hyun,Lu, Shuiyu,Pike, Victor W.
experimental part, p. 4439 - 4447 (2011/10/08)
Effective methods for the introduction of the short-lived positron-emitter fluorine-18 (t1/2 = 109.7 min) at high specific radioactivity into fluoroarenes are valuable for the development of radiotracers for molecular imaging with positron emis
4-ARYLOXYQUINOLIN-2(1H)-ONES AS MTOR KINASE AND PI3 KINASE INHIBITORS, FOR USE AS ANTI-CANCER AGENTS
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Page/Page column 60, (2010/04/06)
4-aryloxyquinolin-2(1H)-ones as mtor kinase and PI3 kinase inhibitors, for use as anti-cancer agents. Compounds of the formula I and pharmaceutically acceptable salts thereof, wherein A, B, R1, R2, R3, R4, R5, R6, and R7 are defined as set forth herein are disclosed. Also disclosed are pharmaceutical compositions comprising the compounds of the invention and a pharmaceutically acceptable carrier, methods of making the compounds of the invention and methods of using the compounds for inhibiting mTOR and PI3 kinases and for treating cancers.
Easy and safe preparations of (diacetoxyiodo)arenes from iodoarenes, with Urea-Hydrogen Peroxide adduct (UHP) as the oxidant and the fully interpreted 1H- and 13C-NMR spectra of the products
Zielinska, Agnieszka,Skulski, Lech
, p. 190 - 194 (2007/10/03)
An easy and safe, though only moderately effective method is presented for preparing (diacetoxyiodo)arenes, ArI(OAc)2, from iodoarenes, ArI, using the commercially available and easily handled urea-hydrogen peroxide adduct (UHP) as the oxidant. The reactions take place in anhydrous AcOH/Ac2O/AcONa (a catalyst) mixtures, at 40°C for 3.5 h to afford the purified ArI(OAc)2 in 37-78% yields. The fully interpreted 1H- and 13C-NMR spectra of the ArI(OAc)2 products are reported.
Unexpected, drastic effect of triflic acid on oxidative diacetoxylation of iodoarenes by sodium perborate. A facile and efficient one-pot synthesis of (diacetoxyiodo) arenes
Hossain, Md. Delwar,Kitamura, Tsugio
, p. 6984 - 6986 (2007/10/03)
An easy, safe, and effective method for preparing (diacetoxyiodo)arenes from iodoarenes is presented. Addition of trifluoromethanesulfonic acid (triflic acid) as a promoter causes a drastic increase in the yield of (diacetoxyiodo)arenes in the reaction of iodoarenes with sodium perborate. The reaction of the iodoarenes with sodium perborate in acetic acid in the presence of triflic acid at 40-45 °C efficiently generates the corresponding (diacetoxyiodo)arenes in high yields within short time.
