- A Practical Procedure for Regioselective Bromination of Anilines
-
A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
- Takahashi, Yusuke,Seki, Masahiko
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p. 1828 - 1832
(2021/04/15)
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- Aryl halide and synthesis method and application thereof
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The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.
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Paragraph 0058-0060
(2020/06/02)
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- Visible-light-promoted oxidative halogenation of (hetero)arenes
-
Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.
- Jiang, Xuefeng,Li, Yiming,Lu, Lingling
-
supporting information
p. 5989 - 5994
(2020/10/18)
-
- NOVEL SUBSTITUTED CYCLOBUTYLBENZENE COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS
-
Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof: (Formula (I)). Also disclosed herein are uses of a compound disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of a composition in the potential treatment or prevention of an IDO-associated disease or disorder.
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Page/Page column 78
(2019/05/02)
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- Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination
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A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.
- Mao, Yang-Jie,Luo, Gen,Hao, Hong-Yan,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
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supporting information
p. 14458 - 14461
(2019/12/09)
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- Synthesis of 2 - fluoro aniline compounds of the method
-
The invention discloses a method for synthesizing 2 - fluoro aniline compounds of the method, the method is: shown in formula Ia aniline compound of formula Ib α and β shown aniline compound as raw materials, through coupling reaction shown [...] azobenzene compound II, then the type II shown azobenzene compound with a palladium catalyst, fluorination reagent, additive, organic solvent, in the 30 - 150 °C temperature closed agitating the fluorination reaction, [...] compound of formula III, type III compounds are shown in the reaction under the action of a reducing [...] shown IV 2 - fluoro aniline compounds; this invention synthetic 2 - fluoro aniline compounds substrate wide adaptability, mild reaction conditions, the operation is simple, fluorinated and good selectivity, [...] aniline compounds is prepared by many drug molecule is an important intermediate and starting material, wide application prospects.
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Paragraph 0116; 0117; 0119; 0120; 0121
(2019/05/15)
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- Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach
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A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.
- Longkumer, Naruti,Richa, Kikoleho,Karmaker, Rituparna,Kuotsu, Visekhonuo,Supong, Aola,Jamir, Latonglila,Bharali, Pranjal,Sinha, Upasana Bora
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p. 276 - 283
(2019/07/12)
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- 2-OXO-THIAZOLE DERIVATIVES AS A2A INHIBITORS AND COMPOUNDS FOR USE IN THE TREATMENT OF CANCERS
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The present invention relates to compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof. The invention further relates to the use of the compounds of Formula (I) as A2A inhibitors. The invention also relates to the use of the compounds of Formula (I) for the treatment and/or prevention of cancer. The invention also relates to a process for manufacturing compounds of Formula (I).
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Page/Page column 137
(2018/10/25)
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- Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A
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Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.
- Zhou, Qingqing,Reekie, Tristan A.,Abbassi, Ramzi H.,Indurthi Venkata, Dinesh,Font, Josep S.,Ryan, Renae M.,Munoz, Lenka,Kassiou, Michael
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p. 5852 - 5869
(2018/11/10)
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- A 4 - bromo - 2 - fluoro aniline the selective synthesis of the method (by machine translation)
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The patented invention has a quaternary ammonium salt produced in situ crosses the bromineneighbouring fluorine aniline production bromide 4 - bromo - 2 - fluoro aniline. Process step its: the quaternary ammonium salt, neighbouring fluorine aniline and solvent are added to a reaction flask, stirring and dissolving, the control temperature is lower than the 30 °C under the condition of, slow instillment bromide, about 30 - 60min drop end, after the temperature of the material to rise to 40 °C left instead on invitation 2.5h; cooling to room temperature, filtered, the filter cake is two times the washing of the solvent, then the filter cake is dispersed in the solvent, then adding 10% of sodium hydroxide solution to pH=7 - 8 and, standing off the aqueous phase, organic uses deionized water to wash two times is to distill the solvent to obtain 4 - bromo - 2 - fluoro aniline. (by machine translation)
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Paragraph 0026-0029
(2017/07/19)
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- Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis
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A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C?H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.
- Mostafa, Mohamed A. B.,Calder, Ewen D. D.,Racys, Daugirdas T.,Sutherland, Andrew
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supporting information
p. 1044 - 1047
(2017/02/05)
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- NOVEL COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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Provided are a compound for an organic light emitting device and an organic light emitting device comprising the same. To this end, it is possible to provide a compound for an organic light emitting device which can be used as a host, a hole-transport material, or an electron-transport material capable of enhancing light-emitting efficiency of phosphorescent light-emitting materials by having outstanding electrical stability, an electron and hole transportability, and a high level of triplet state energy, and the organic light emitting device.
- -
-
Paragraph 0119-0121; 0216-0218
(2016/10/10)
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- Pyrazolo[3,4-c]pyridine derivative
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The invention relates to a pyrazolo[3,4-c]pyridine derivative. The invention relates to a compound represented by a formula (I), a tautomer thereof, an optical isomer thereof or a pharmaceutically acceptable salt thereof, wherein the formula (I) is shown in the description, and Z, X, RNc, RNd, RNe and RNf are defined according to the claim 1. The invention further relates to the pharmaceutical composition contain the compound. The invention further relates to use of the compound or the pharmaceutical composition in preparing a drug for preventing and/or treating a disease which inhibits positive influence of an Xa factor, particularly use in preparing the drug for preventing and/or treating the disease which inhibits positive influence of the Xa factor under the condition of low hemorrhage risk.
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-
Paragraph 0266; 0267; 0268
(2016/10/08)
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- Hexamethonium bis(tribromide) (HMBTB) a recyclable and high bromine containing reagent
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A recyclable and high bromine containing di-(tribromide) reagent, hexamethonium bis(tribromide) (HMBTB) has been synthesized and utilized for the bromination of various organic substrates. The spent reagent hexamethonium bromide (HMB) can be effectively recycled by regenerating and reusing it without significant loss of activity. The crystalline and stable bis(tribromide) is an effective storehouse of very high percentage of active bromine requiring just half an equivalent of it for complete bromination. Both the Br3- moieties in HMBTB are nearly linear with Br-Br-Br angle of 179.55°.
- Paul, Bappi,Bhuyan, Bishal,Purkayastha, Debraj D.,Dhar, Siddhartha S.,Patel, Bhisma K.
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p. 5646 - 5650
(2015/09/21)
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- Regioselective chlorination and bromination of unprotected anilines under mild conditions using copper halides in ionic liquids
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By using ionic liquids as solvents, the chlorination or bromination of unprotected anilines at the para-position can be achieved in high yields with copper halides under mild conditions, without the need for potentially hazardous operations such as supplementing oxygen or gaseous HCl.
- Wang, Han,Wen, Kun,Nurahmat, Nurbiya,Shao, Yan,Zhang, He,Wei, Chao,Li, Ya,Shen, Yongjia,Sun, Zhihua
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supporting information; experimental part
p. 744 - 748
(2012/06/30)
-
- Synthesis and reactivity studies of a new reagent, ethyltriphenylphosphonium tribromide
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A new reagent, ethyltriphenyl phosphonium tribromide (ETPPTB), has been synthesized and studied. Results show that the reagent is quite efficient for various reactions such as organic bominations, acylations, and isothiocyanate preparation. Copyright
- Jamir, Latonglila,Alimenla,Kumar, Anil,Sinha, Dipak,Sinha, Upasana B.
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experimental part
p. 147 - 155
(2011/03/17)
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- Discovery of potent and selective urea-based ROCK inhibitors and their effects on intraocular pressure in rats
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A series of urea-based Rho kinase (ROCK) inhibitors were designed and evaluated. The discovered compounds had excellent enzyme and cellular potency, high kinase selectivity, high aqueous solubility, good porcine corneal penetration, and appropriate DMPK profiles for topical applications as antiglaucoma therapeutics.
- Yin, Yan,Cameron, Michael D.,Lin, Li,Khan, Susan,Schroeter, Thomas,Grant, Wayne,Pocas, Jennifer,Chen, Yen Ting,Schuerer, Stephan,Pachori, Alok,Lograsso, Philip,Feng, Yangbo
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scheme or table
p. 175 - 179
(2010/10/21)
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- Ferrous sulfide/aqueous ammonia: Simple, efficient, and chemoselective reagent for the conversion of aromatic azide to amine
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A practical, environmentally benign, rapid, and efficient method for the reduction of aromatic azide to amine is described using FeS/aqueous ammonia in the presence of other reducible functionalities. Application of a novel reducing reagent results in aromatic amines with excellent yield and high chemoselectivity, without need of any purification techniques. Copyright Taylor & Francis Group, LLC.
- Gadakh, Amol V.,Karale, Bhausaheb K.
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p. 186 - 191
(2008/03/17)
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- In search of simplicity and flexibility: A rational access to twelve fluoroindolecarboxylic acids
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All twelve indolecarboxylic acids 1-12 carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles 13-16 or from the chlorinated derivatives 22, 23 and 25 by hydrogen/metal permutation ("metalation"), or from the bromo- or iodofluoroindoles 17-20 and 26, 27, 29 and 30 by halogen/metal permutation, the organometallic intermediate being each time trapped with carbon dioxide. In most, though not all cases, the nitrogen atom in the five-membered ring had to be protected by a trialkylsilyl group. Some of the bromo- or iodofluoroindoles (26 and 27) were successfully subjected to a basicity gradient-driven selective migration of the heavy halogen. An unexpected finding on the way to the target compounds were the rigorously site-selective metalation of the 5-fluoro-N-(trialkylsilyl)indole (14b; exclusive deprotonation of the 4-position). The fluoroindoles 13-16, although previously known, were accessed more conveniently from suitably substituted nitrobenzenes using the Bartoli or the Leimgruber-Batcho method. A new and very attractive indole synthesis was elaborated consisting of the ortho-lithiation of an N-acyl-protected aniline followed by ortho-formylation, Wittig chloromethylenation and base-catalyzed cyclization accompanied by dehydrochlorination. These five consecutive steps can be contracted to a convenient one-pot protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Schlosser, Manfred,Ginanneschi, Assunta,Leroux, Frederic
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p. 2956 - 2969
(2007/10/03)
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- Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
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(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
- Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
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p. 2870 - 2873
(2007/10/03)
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- A new recyclable ditribromide reagent for efficient bromination under solvent free condition
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1,2-Dipyridiniumditribromide-ethane (DPTBE) has been synthesized and explored as a new efficient brominating agent. The crystalline ditribromide reagent is stable for months and acts as a safe source of bromine requiring just 0.5 equiv for complete bromination. It has high active bromine content per molecule and shows a remarkable reactivity compared to other tribromide reagents toward various substrates by just grinding the reagent and substrates in a porcelain mortar at room temperature. No organic solvent has been used during any stage of the reaction for substrates giving product as solid. Product can easily be isolated by just washing the highly water soluble 1,2- dipyridiniumdibromide-ethane (DPDBE) from the brominated product. The spent reagent can be recovered, regenerated, and reused without any significant loss.
- Kavala, Veerababurao,Naik, Sarala,Patel, Bhisma K.
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p. 4267 - 4271
(2007/10/03)
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- Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate
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The selective monobromination of various deactivated anilines using potassium bromide and sodium perborate as oxidant has been achieved. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities. (C) 2000 Elsevier Science Ltd.
- Roche, Didier,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
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p. 2083 - 2085
(2007/10/03)
-
- Halogenation of aromatic amine compounds
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Aromatic amine compounds are halogenated in the presence of a quaternary ammonium halide.
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- Catalytic bromination of 2-fluoroaniline
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A process for the production of 2,4-dihaloaniline, especially 4-bromo-2-fluoroaniline, via the halogenation (bromination) of 2-haloaniline (2-fluoroaniline) in the presence of quaternary ammonium halide (bromide) catalyst in an inert solvent. The yield and selectivity are very high and the inventive method includes continuous processing with recycle of the catalyst/solvent mixture.
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- The Synthesis and Transition Temperatures of Some Fluoro-Substituted 4-Cyanophenyl and 4-Cyanobiphenyl-4'-yl 4-Pentyl- and 4-Butoxy-Benzoates
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A series of 4-cyanophenyl 4-X-benzoates and a series of 4-cyanobiphenyl-4'-yl 4-X-benzoates (X= pentyl, butoxy) have been prepared without fluoro-substitution and with mono-fluoro to tetra-fluoro-substitution; all possible combinations of substitution patterns at the positions ortho- to the cyano group and ortho- to the carboxylate group have been obtained in an attempt to determine the structural features which are responsible for some members of these series showing very large positive values of dielectric anisotropy.The synthesis of novel precursors required for the preparation of these esters is described and the melting points and transition temperatures of the esters are discussed and an explanation is provided for the variation of Tn-1 values with position and extent of fluoro-substitution. - Keywords: Fluoro-substitution, phenyl and biphenyl benzoates, terminal cyano namatogens.
- Gray, G. W.,Hird, M.,Lacey, D.,Toyne, K. J.
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p. 165 - 190
(2007/10/02)
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- Tetrahydrophthalamide derivatives
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Novel tetrahydrophthalamide derivatives of the general formula: STR1 wherein X is chlorine or bromine, and R is hydrogen, or an alkyl, a substituted alkyl, a cycloalkyl, a substituted cycloalkyl, an alkenyl, or an alkynyl group, have strong herbicidal activity and are particularly, useful for selectively controlling weeds without causing any substantial injury to soybean and other crop plants.
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- Substituted amino acids
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Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.
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- Cycloalkanapyrazole-3-carbonitrile herbicides
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Herbicidal cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; X is fluorine, chlorine, bromine, iodine, cyano, or methoxy; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy; provided that (a) when n is 3, R1 must be hydrogen; (b) when n is 5, R1 must be hydrogen, Y must be hydrogen or fluorine, Z and V must both be hydrogen, and X must be fluorine, chlorine or bromine; (c) when V is methoxy, X and Y must be chlorine, and Z must be hydrogen; and (d) when V is fluorine or chlorine, X must be fluorine, chlorine or bromine, and Z must be hydrogen.
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- Cycloalkanapyrazole herbicides
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Herbicidal cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; Q is fluorine, chlorine, bromine or iodine; X is fluorine, chlorine, bromine, iodine, cyano, methoxy or nitro; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy with the proviso that A. when n is 5, R1 must be hydrogen, Q must be chlorine or bromine, Z and V must both be hydrogen and Y must be hydrogen or fluorine; B. when n is 3 or 4 and Q is fluorine or iodine, R1, Z and V must be hydrogen and Y must be hydrogen or fluorine; C. when n is 3 and R1 is methyl, Q must be chlorine or bromine, Y must be hydrogen or fluorine and Z and V must both be hydrogen; and, D. when V is other than hydrogen, X must be fluorine, chlorine or bromine and Z must be hydrogen.
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- Herbicidal 2-(substituted aryl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-diones
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This invention relates to herbicidal 2-(substituted aryl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-diones. These compounds may be used for selective weed control for certain crops or for total vegetation control. In particular, the compounds may be utilized as rice herbicides and have the formula SPC1 Wherein X is Cl, Br or F, and Y is H or F, provided that when Y is F, X is F.
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- Herbicidal isoindol-1-one derivatives
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This invention relates to herbicidal isoindol-1-one derivatives. These compounds have the general formulae: SPC1 Wherein R1 is hydrogen or methyl; R2 is hydrogen or alkyl of 1 to 4 carbons; X is fluorine, chlorine or bromine; Y is hydrogen or fluorine; Z is hydrogen or fluorine, provided that when Y and Z are both fluorine, X must also be fluorine; and A is --(CH2)4 -- or --CH=CH--CH=CH--, provided that when A is --CH=CH--CH=CH-- and Y is hydrogen, Z must be fluorine. Both geometric isomers, Formulae IIa and IIb, are encompassed by this invention. In particular, these compounds have demonstrated that they are active pre- and post-emergence herbicides and tend to do minimal damage to certain desirable crops, e.g., corn and wheat.
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- 2-Aryl-5,6,7,8-tetrahydroimidazo[1,5a]-pyridine-1,3(2H,8aH)-diones as herbicides
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This invention relates to novel 2-Aryl-5,6,7,8-tetrahydroimidazo[1,5a]-pyridine-1,3(2H,8aH)-diones and their use as herbicides. These novel compounds may be used for selective weed control in certain crops or for total vegetation control.
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- Herbicidal isobenzofuranones
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This invention relates to herbicidal isobenzofuranones. These compounds may be used for selective weed control in certain crops or for total vegetation control.
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