- NEW COMPOUND
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PROBLEM TO BE SOLVED: To provide a new compound that does not have structural similarity to ceramide and has excellent CERT inhibitory activity. SOLUTION: The present invention provides a new compound of structural formula (I). A bond group -X- is cis-cyclopropyl-, R1, R2, R3, R4, and R5 independently represent a hydrogen atom, a halogen atom, a linear or branched C1-C8 alkyl group that may have a halogen atom, or OR6. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0316; 0326
(2019/11/26)
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- A simple and efficient two-step synthesis of 1,2,3-triiodoarenes via consecutive C-H iodination/ipso-Iododecarboxylation strategy: A potential application towards Ortho-diiodoarenes by Regioselective metal-iodine exchange reaction
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A general, robust, and efficient method for the conversion of benzoic acids to 1,2,3-triiodoarenes and 1,2,3-trihaloarenes via a two-step synthesis is reported. Commercially available benzoic acids were used that can allow the reactions to be performed on multi-gram scales with good-to-excellent yields. This report discloses a practical method for the synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, scalable, and easy to workup and purify. A potential application of the target compounds as precursors for novel regioselective metal-iodine exchange reaction of 1,2,3-triiodoarenes was also demonstrated. It provided ortho-diiodoaryl derivatives in a high regioselective fashion that are useful intermediates in synthesis and indeed are hard to synthesize by any other means.
- Al-Zoubi, Raed M.,Al-Mughaid, Hussein,McDonald, Robert
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p. 912 - 918
(2015/06/25)
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- Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
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The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.
- Li, Lu,Liu, Wenbo,Zeng, Huiying,Mu, Xiaoyue,Cosa, Gonzalo,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 8328 - 8331
(2015/07/15)
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- Tetraflic acid (1,1,2,2-Tetrafluoroethanesulfonic acid, HC 2F4SO3H) and gallium tetraflate as effective catalysts in organic synthesis
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Tetraflic acid offers ample acidity for various organic reactions that require high acidity. Its gallium(III) salt is an efficient catalyst under mild condtions for synthetic transformations such as the ketonic Strecker reaction for the synthesis of fluorinated α-amino nitriles and condensation- cyclzation reactions using suitable fluoro ketones and 1,2-disubstituted benzenes for the direct preparation of 5-membered or 6-membered fluorinated heterocycles. Copyright
- Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Kulkarni, Aditya,Olah, George A.,Harmer, Mark A.
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p. 2163 - 2171
(2012/11/07)
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- Synthesis and biological evaluation of 3-aryltyramines as fragments binding to BACE-1 and BACE-2
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3-Aryltyramines were prepared in one single step from tyramine and various arenediazonium salts by radical arylation. Binding as well as enzyme inhibition data of the 14 compounds do not prove true interaction with BACE-1. In contrast, with BACE-2 inhibition and binding could be confirmed indicating that 3-aryltyramines are potential starting points for a drug discovery effort.
- Fehler, Stefanie K.,Pratsch, Gerald,Huber, Walter,Gast, Alain,Hochstrasser, Remo,Hennig, Michael,Heinrich, Markus R.
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supporting information; experimental part
p. 2189 - 2194
(2012/05/20)
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- PROCESS FOR PREPARING AROMATIC IODINE COMPOUNDS
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The present invention relates to a process for preparing iodinated aromatic compounds. Particularly, the present invention comprises the step of performing the iodination of a non-halogenated aromatic compound, a monoiodo aromatic compound, a diiodo aromatic compound, and iodine in the presence of a zeolite catalyst under oxygen atmosphere. In the process for preparing iodinated aromatic compounds according to the present invention, an iodination and an iodine conversion simultaneously occur, and then prevent side-reactions. Also, the lifetime of an iodination catalyst used therein can be extended by controlling the reaction temperature stably. Therefore, the process can be used for mass production of diiodo compound.
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Page/Page column 7-8
(2011/10/19)
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- PROCESS FOR THE PREPARATION OF IODIDES
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This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.
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Page/Page column 35
(2012/01/05)
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- PROCESS FOR PREPARING IODINATED AROMATIC COMPOUNDS
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The present invention relates to a process for preparing iodinated aromatic compounds. Particularly, the present invention comprises the step of performing the iodination of a non-halogenated aromatic compound, a monoiodo aromatic compound, a diiodo aromatic compound, and iodine in the presence of a zeolite catalyst under oxygen atmosphere. In the process for preparing iodinated aromatic compounds according to the present invention, an iodination and an iodine conversion simultaneously occur, and then prevent side-reactions. Also, the lifetime of an iodination catalyst used therein can be extended by controlling the reaction temperature stably. Therefore, the process can be used for mass production of diiodo compound.
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Page/Page column 5
(2011/10/13)
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- Metal-free efficient, general and facile iododecarboxylation method with biodegradable co-products
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The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N-iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co-product is removed as a water-soluble biodegradable material. Copyright
- Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
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supporting information; experimental part
p. 1438 - 1442
(2011/07/30)
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- MANUFACTURING PROCESS FOR IODINATED AROMATIC COMPOUNDS
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Disclosed is a method for preparing an iodinated aromatic compound. More specifically, disclosed is a method of preparing an iodinated aromatic compound by iodinating an aromatic compound in the presence of oxygen over a zeolite catalyst, in which the aromatic compound and its monoiodo compound, as raw materials, are allowed to react with iodine. In comparison with a method in which only the aromatic compound is used as a raw material without adding the monoiodo compound, the disclosed method can increase the productivity of diiodo compounds and the selectivity to a p-diiodo compound and, at the same time, suppress side reactions, thus lengthening the life span of the catalyst.
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Page/Page column 3
(2010/08/07)
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- MANUFACTURING PROCESS FOR IODINATED AROMATIC COMPOUNDS
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Disclosed is a method for preparing an iodinated aromatic compound. More specifically, disclosed is a method of preparing an iodinated aromatic compound by iodinating an aromatic compound in the presence of oxygen over a zeolite catalyst, in which the aromatic compound and its monoiodo compound, as raw materials, are allowed to react with iodine. In comparison with a method in which only the aromatic compound is used as a raw material without adding the monoiodo compound, the disclosed method can increase the productivity of diiodo compounds and the selectivity to a p-diiodo compound and, at the same time, suppress side reactions, thus lengthening the life span of the catalyst.
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Page/Page column 9-10
(2009/05/30)
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- METHOD OF PREPARING IODINATED AROMATIC COMPOUNDS
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The present invention relates to a method of preparing iodinated aromatic compounds, and more preferably a method of preparing iodinated aromatic compounds comprising a step of iodinating a react ant including an aromatic compound, a di-iodo aromatic compound or water, and iodine (I2) in the presence of a zeolite catalyst and oxygen. The method of the present invention has an advantage that by iodination of a reactant including the aromatic compound, and the di~ iodo aromatic compound or water in the presence of the zeolite catalyst and oxygen, the temperature of the iodinating reactor can be controlled reliably and constantly, thereby resulting in improved productivity per unit weight of catalyst and inhibition of a side reaction in accordance with suppression of producing impurities. In addition, the productivity of the iodinated aromatic compound, preferably the di-iodo aromatic compound, more preferably a p-di-iodo aromatic compound can be improved, and thus can be widely used in the preparation of a di-iodo aromatic compound such as a p-di-iodo aromatic compound.
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Page/Page column 17-18; 19
(2009/07/18)
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- Synthesis of low generation phenylenealkylene dendrons as nonpolar building blocks for a dendrimer construction set
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The gram scale syntheses of first and second generation (G1 and G2) dendrons 1-4, and 35, based on aryl and alkyl moieties, by Suzuki-Miyaura cross-coupling are presented. Both a divergent and an accelerated convergent route are applied. In addition, first results on the synthesis of hyperbranched oligomers of AB2 monomer 19 are reported.
- Beinhoff, Matthias,Karakaya, Birol,Schlüter, A. Dieter
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- EPR probes with well-defined, long distances between two or three unpaired electrons
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The synthesis of rod- and star-shaped compounds carrying two or three spin labels as end groups is described. The unpaired electrons are 2.8-5.1 nm apart from each other. The shape-persistent scaffolds were obtained through Pd-Cu-catalyzed alkynyl-aryl coupling and Pd-Cu-catalyzed, alkyne dimerization in the presence of oxygen using p-phenyleneethynylene as the basic shape-persistent building block. The spin label 1-oxyl-2,2,5,5-tetramethylpyrroline-3-carboxylic acid (4) was attached through esterification of the terminal phenolic OH groups of the scaffold.
- Godt,Franzen,Veit,Enkelmann,Pannier,Jeschke
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p. 7575 - 7582
(2007/10/03)
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- Novel Homologation Reaction of Arylzincates Bearing a Leaving Group at the Ortho and Meta Positions
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Arylzincates bearing a leaving group at the ortho, meta, and para positions were generated by iodine/zinc exchange reaction of the corresponding iodoaryl sulfonates with Bu3ZnLi, and their reactivity was investigated via product analysis after hydrolysis and treatment with iodine. Zincates derived from o-iodophenyl triflates and tosylate underwent homologation reaction to give o-butylphenylzinc species. o-Benzyne as an intermediate of the reaction was demonstrated by the lack of regioselectivity for trisubstituted zincates. Zincates derived from m-iodophenyl triflates also underwent homologation leading to m-butylphenylzinc species. Similar product ratios observed in the reactions of regioisomeric trisubstituted iodophenyl triflates as well as the formation of radical reaction byproducts suggested the involvement of m-benzyne intermediate. p-(Trifluoromethane-sulfonyloxy)phenylzincate was thermally stable at room temperature; generation of p-benzyne was not observed.
- Harada, Toshiro,Chiba, Minako,Oku, Akira
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p. 8210 - 8213
(2007/10/03)
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- Nitrogen dioxide - Sodium iodide as an efficient reagent for the one- pot conversion of aryl amines to aryl iodides under nonaqueous conditions
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Successive treatment of aromatic amines with liquid nitrogen dioxide and powdered sodium iodide in acetonitrile at -20 °C, followed by usual work- up, gave the corresponding aryl iodides in good yield. This method worked especially well for less basic amines bearing electron-withdrawing substituents.
- Suzuki, Hitomi,Nonoyama, Nobuaki
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p. 4533 - 4536
(2007/10/03)
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- Syntheses of various 5-(3′-substituted phenyl)uracils
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The Suzuki Pd(0)-catalysed coupling between arylboronic acids and aryl bromides or iodides in weakly alkaline medium has been used for the preparation of 5-(3′-chlorophenyl)-, 5-(3′-iodophenyl)-, 5-(3′-aminophenyl)-, 5-(3′-azidophenyl)-, 5-(3′-methylthiophenyl)- and 5-(3′-styryl)-substituted 2,4-di-t-butoxypyrimidines. In the coupling between 2,4 di-t-butoxy-5-pyrimidineboronic acid and the six different aryl halides that were used as coupling partners, only 1-azido-3-bromobenzene did not give satisfactory yields, 18%. The other five aryl halides gave the desired 5-(3′-substituted phenyl)-2,4-di-t-butoxypyrimidines in 41-92% yield. Dealkylation of these five 5-(3′-substituted phenyl)-2,4-di-t-butoxypyrimidines in 2.5M hydrochloric acid gave the corresponding 5-(bromoaryl)uracils in almost quantitative yields. 5-(3′-Azidophenyl)uracil was prepared in 43% yield directly from 5-(3′-aminophenyl)-2,4-di-t-butoxypyrimidine.
- Wellmar, Ulf,Hoernfeldt, Anna-Britta,Gronowitz, Salo
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p. 409 - 414
(2007/10/03)
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- Vapour-phase Chemistry of Arenes. Part 13. Reactivity and Selectivity in the Gas-phase Reactions of Hydroxyl Radicals with Monosubstituted Benzenes at 563 K
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The reactions of hydroxyl radicals with benzene derivates C6H5Z (Z = H, Me, F, Cl, Br, I, CF3, or CN) have been studied in a flow reactor at 563 K in nitrogen, using the thermolysis of ButOOH as a source of .OH.Under these conditions there are two product-forming pathways.The major one involves hydrogen abstraction to give aryl radicals ZC6H4. (II) as the first step; depending on Z, its displacement to form phenol may also occur.Relative rates for hydrogen abstraction were determined in competition experiments using side-chain hydrogen abstraction from added toluene as a reference.This resulted in the order (for Z =): 1,8(Me), 1.0(H), 0.47(F), 0.29(Cl), 0.34(CF3), 0.20(CN), consonant with the electrophilic nature of .OH.The site selectivity of hydrogen abstractions was determined by scavenging part of the aryl radicals (II) with iodine.A Hammett plot, using ? constants for meta and para positions, led to ρ -1.0.The features of hydrogen abstraction by .OH are discussed and compared with those for the analogous reaction of Cl.The formation of phenol was found to decrease in importance in the order F, Cl, Br, and I.This result is rationalized on a thermochemical kinetic basis.
- Mulder, Peter,Louw, Robert
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p. 1167 - 1174
(2007/10/02)
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