13298-50-5Relevant articles and documents
Multi-stimuli-responsive fluorescence of axially chiral 4-ene-β-Diketones
Wu, Dehua,Fang, Xinyi,Song, Jintong,Qu, Lang,Zhou, Xiangge,Xiang, Haifeng,Wang, Jun,Liu, Jin
, (2021)
A unique series of simple, smart, and chiral binaphthalene-substituted 4-ene-β-diketones molecules has been designed and prepared. Their optical properties, charge contribution, and transition process highly depend on their chemical structures. These π-conjugated materials are highly emissive in both solution and solid (emission quantum yield up to 68%), owing to the inhibition of enol-keto tautomerization and the effect of steric hindrance from binaphthalene. Through ethylenic bond hydrolysis, they can be used for not only cation/anion sensing but also chiral amino acids recognition. Moreover, at low concentrations, they have little cytotoxicity to living cells and can stain cytoplasm. Therefore, they afford a new platform in the design of multi-stimuli-responsive, smart, and chiral materials.
Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds
Liang, Taoyuan,Zhao, He,Gong, Lingzhen,Jiang, Huanfeng,Zhang, Min
, p. 6736 - 6740 (2019)
Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.
I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives
An, Zhenyu,Liu, Yafeng,Yan, Rulong,Zhao, Pengbo
supporting information, p. 3240 - 3244 (2021/06/16)
An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).
Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors
Yao, Haiyan,Guo, Quanping,Wang, Mengran,Wang, Rui,Xu, Zhaoqing
, (2021/08/25)
Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.
Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction
He, Jian-Ping,Huang, Guo-Sheng,Luo, Nan,Zhan, Zhen-Zhen,Zhang, Ming-Ming
supporting information, p. 9831 - 9835 (2021/01/05)
We have developed a copper-mediated one-pot synthesis of 2,3,5-trisubstituted pyrroles from 1,3-dicarbonyl compounds and acrylates using ammonium acetate as a nitrogen source. The reaction achieves C-C and C-N bond formation and provides an efficient approach to access highly functionalized pyrroles without further raw material preparation. This method is operationally simple, compatible with a wide range of functional groups, and provides the target products in moderate to good yields. This journal is
Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
supporting information, p. 4179 - 4188 (2019/05/08)
Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide
Rajasekar, Shanmugam,Anbarasan, Pazhamalai
supporting information, p. 4563 - 4567 (2019/11/03)
An efficient proline-catalyzed synthesis of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles has been accomplished from 1,3-dicarbonyl compounds and sulfonyl azides. The developed reaction is suitable for various symmetrical and unsymmetrical 1,3-dicarbonyl compounds, tolerates various functional groups and affords 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles in good yield with excellent regioselectivity. Rhodium-catalyzed denitrogenative functionalization of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles further demonstrates their utility in organic synthesis.
Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
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Paragraph 0028, (2018/07/10)
The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.
Palladium-catalysed carbonylative α-arylation of acetone and acetophenones to 1,3-diketones
Schranck, Johannes,Tlili, Anis,Alsabeh, Pamela G.,Neumann, Helfried,Stradiotto, Mark,Beller, Matthias
supporting information, p. 12624 - 12628 (2013/10/01)
Three COmponent α-arylation: A carbonylative ketone α-arylation process employing acetone for the first time, as well as acetophenones, is described (see scheme). The reaction tolerates a range of (hetero)aryl iodides and several functionalised aryl ketone coupling partners. Only low pressures of molecular CO are applied and no additional solvent is necessary. Copyright
Albumin-directed stereoselective reduction of 1,3-diketones and β-hydroxyketones to anti diols
Berti, Federico,Bincoletto, Simone,Donati, Ivan,Fontanive, Giampaolo,Fregonese, Massimo,Benedetti, Fabio
experimental part, p. 1987 - 1999 (2011/04/25)
The reduction of 1,3-diketones and β-hydroxyketones with NaBH 4 in aqueous acetonitrile is highly stereoselective in the presence of stoichiometric amounts of bovine or human albumin, giving anti 1,3-diols with d.e. up to 96%. The same reaction, without albumin, gives syn and anti 1,3-diols in approximately 1:1 ratio. The presence of an aromatic carbonyl group is essential for diastereoselectivity in the NaBH4/albumin reduction of both 1,3-diketones and β-hydroxyketones. Thus, 3-hydroxy-1-(p-tolyl)-1- butanone is stereoselectively reduced in the presence of albumin, while reduction of its isomer 4-(p-tolyl)-4-hydroxy-2-butanone is not stereoselective. The albumin-controlled reduction is not stereospecific as both enantiomers of 1-aryl-3-hydroxy-1-butanones are reduced to diols with identical stereoselectivities. Circular dichroism of the bound substrates confirms that aromatic ketones are recognized by the protein's IIA binding site. Binding studies also suggest that 1,3-diketones are recognized in their enol form. From the effect of pH on binding of a diketone it is concluded that, in the complex with the substrate, ionizable residues His242 and Lys199 are in the neutral and protonated forms, respectively. A homology model of BSA was obtained and docking of model substrates confirms the preference of the protein for aromatic ketones. Modelling of the complexes with the substrates also allows us to propose a mechanism for the reduction of 1,3-diketones in which the chemoselective reduction of the first (aliphatic) carbonyl is followed by the diastereoselective reduction of the second (aromatic) carbonyl. The role of albumin is thus a combination of chemo- and stereocontrol.
