126550-93-4Relevant academic research and scientific papers
Structure of and Electronic Interactions in Aromatic Polyvalent Iodine Compounds: a 13C NMR Study
Katritzky, Alan R.,Gallos, John K.,Durst, H. Dupont
, p. 815 - 822 (1989)
Available data on the structures, electronic substituent effects and 13C NMR spectra of aromatic polyvalent iodine compounds, particularly iodoso and iodoxy derivatives, are summarized and discussed.A series of aromatic tri- and penta-valent iodine compou
A practical route for synthesizing a PET ligand containing [18F]fluorobenzene using reaction of diphenyliodonium salt with [18F]F-
Zhang, Ming-Rong,Kumata, Katsushi,Suzuki, Kazutoshi
, p. 8632 - 8635 (2007)
The aim of this study was to develop a practical route for preparing a fluorine-18 ([18F]) labelled ligand ([18F]1) containing [18F]fluorobenzene ring by employing the reaction of diphenyliodonium salt with [18F]F-. Diphenyliodonium tosylate (2) was synthesized from tributylphenylstannyl compound (6) with [hydroxy(tosyloxy)iodo]benzene (7). Using this method, [18F]DAA1106 ([18F]3a), a positron emission tomography ligand for imaging peripheral-type benzodiazepine receptor, was prepared.
A Potential PET Radiotracer for the 5-HT2C Receptor: Synthesis and in Vivo Evaluation of 4-(3-[18F]fluorophenethoxy)pyrimidine
Kim, Juhyeon,Moon, Byung Seok,Lee, Byung Chul,Lee, Ho-Young,Kim, Hak-Joong,Choo, Hyunah,Pae, Ae Nim,Cho, Yong Seo,Min, Sun-Joon
, p. 996 - 1003 (2017)
The serotonin 2C receptor subtype (5-HT2C) is an excitatory 5-HT receptor widely distributed throughout the central nervous system. As the 5-HT2C receptor displays multiple actions on various neurotransmitter systems including glutamate, dopamine, epinephrine, and γ-aminobutyric acid (GABA), abnormalities of the 5-HT2C receptor are associated with psychiatric diseases such as depression, schizophrenia, drug abuse, and anxiety. Up to date, three kinds of 5-HT2C PET radiotracers such as [11C]N-methylated arylazepine (1), [11C]WAY-163909 (2), and [18F]fluorophenylcyclopropane (3) have been developed, but they may not be suitable for in vivo 5-HT2C imaging study due to their modest specific binding. Herein, the synthesis and in vivo evaluation of 4-(3-[18F]fluorophenethoxy)pyrimidine [18F]4 as a potential PET radiotracer for the 5-HT2C receptor is described. [18F]4 was synthesized by nucleophilic aromatic substitution of diaryliodonium precursor 17a with a 7.8 ± 2.7% (n = 6, decay corrected) radiochemical yield and over 99% radiochemical purity, showing an 89 ± 14 GBq/μmol specific radioactivity. The in vivo PET imaging studies of [18F]4 with or without lorcaserin, a U.S. Food and Drug Administration approved selective 5-HT2C agonist, demonstrated that [18F]4 exhibits a high level of specific binding to 5-HT2C receptors in the rat brain.
Convenient synthesis of diaryliodonium salts for the production of [18F]F-DOPA
Edwards, Richard,Westwell, Andrew D.,Daniels, Stephen,Wirth, Thomas
supporting information, p. 625 - 630 (2015/01/30)
[18F]F-DOPA is an important radiotracer that is used in the diagnosis of Parkinson's disease and neuroendocrine tumours. We describe a simple synthesis for a number of diaryliodonium salt precursors that are suitable for the production of [18F]F-DOPA through reaction with no carrier added (n.c.a.) nucleophilic [18F]fluoride. The simple procedure gives bench-stable, complex iodonium precursors in good yields without the need for laborious anhydrous conditions. Further alteration to the precursor counterion can be readily achieved for a range of halides and pseudo halides by a simple modification of the workup. Preliminary "hot" and "cold" fluorination results show the suitability of the compounds for the production of [18F]F-DOPA.
Regiospecific syntheses of functionalized diaryliodonium tosylates via [hydroxy(tosyloxy)iodo]arenes generated in situ from (diacetoxyiodo)arenes
Chun, Joong-Hyun,Pike, Victor W.
experimental part, p. 1931 - 1938 (2012/04/17)
Ready access to 18F-labeled aryl synthons is required for preparing novel radiotracers for molecular imaging with positron emission tomography. Diaryliodonium salts react with cyclotron-produced no-carrier-added [18F]fluoride ion to
Approach to the synthesis of indoline derivatives from diaryliodonium salts
Landge, Kamalkishor P.,Jang, Keun Sam,Lee, Sang Yeul,Chi, Dae Yoon
experimental part, p. 5705 - 5713 (2012/09/07)
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.
Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides
Merritt, Eleanor A.,Carneiro, Vania M. T.,Silva Jr., Luiz F.,Olofsson, Berit
experimental part, p. 7416 - 7419 (2011/02/22)
The first one-pot synthesis of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs) from iodine and arenes is presented, thereby avoiding the need for expensive iodine(III) precursors. A large set of HTIBs, including a polyfluorinated analogue, can be obtained from the corresponding aryl iodide under the same conditions. The reaction proceeds under mild conditions, without excess reagents, and is fast and high-yielding. Together, the two presented routes give access to a wide range of HTIBs, which are useful reagents in a variety of synthetic transformations.
Aryliodonium derivatives of 2-amino-1,4-quinones: Preparation and reactivity
Papoutsis, Ioannis,Spyroudis, Spyros,Varvoglis, Anastasios,Raptopoulou, Catherine P.
, p. 6097 - 6112 (2007/10/03)
The reaction of 2-amino-1,4-quinones with [(hydroxy)(tosyloxy)iodo]arenes affords stable 2-amino-3-aryliodonio-1,4- quinones in high yields. The latter, upon treatment with alkali, are converted to the corresponding zwitterionic 3-aryliodonio-1,4-quinone-2-imides. This new class of compounds exhibits an interesting reactivity: upon heating, aryl migration from iodine to nitrogen is observed, while photochemical reaction with aromatic compounds and 2,3-dihydrofuran leads to substitution products. Nucleophilic attack of sodium alkoxides on these zwitterions results in opening of the quinone ring affording synthetically interesting multifunctional products.
