- Synthesis of Highly Substituted Biaryls by the Construction of a Benzene Ring via in Situ Formed Acetals
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Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Br?nsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.
- Balamurugan, Rengarajan,Manojveer, Seetharaman,Tarigopula, Chandrahas
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p. 11871 - 11883
(2021/09/13)
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- I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives
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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.).
- An, Zhenyu,Liu, Yafeng,Yan, Rulong,Zhao, Pengbo
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supporting information
p. 3240 - 3244
(2021/06/16)
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- Multi-stimuli-responsive fluorescence of axially chiral 4-ene-β-Diketones
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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.
- Wu, Dehua,Fang, Xinyi,Song, Jintong,Qu, Lang,Zhou, Xiangge,Xiang, Haifeng,Wang, Jun,Liu, Jin
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- Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors
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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.
- Guo, Quanping,Wang, Mengran,Wang, Rui,Xu, Zhaoqing,Yao, Haiyan
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- Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction
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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
- He, Jian-Ping,Huang, Guo-Sheng,Luo, Nan,Zhan, Zhen-Zhen,Zhang, Ming-Ming
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supporting information
p. 9831 - 9835
(2021/01/05)
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- 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
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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.
- Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
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supporting information
p. 4179 - 4188
(2019/05/08)
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- Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
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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.
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Paragraph 0024
(2018/07/10)
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- Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans
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Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.
- Marichev, Kostiantyn O.,Wang, Yi,Carranco, Alejandra M.,Garcia, Estevan C.,Yu, Zhi-Xiang,Doyle, Michael P.
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p. 9513 - 9516
(2018/08/28)
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- O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
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A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
- Katrun, Praewpan,Songsichan, Teerawat,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
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supporting information
p. 1109 - 1121
(2017/02/24)
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- H2O2-promoted reactions of aliphatic primary amines with 1,3-diketones for the synthesis of 1 H -pyrrol-3(2 H)-ones at ambient temperature in water
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A green organic reaction of aliphatic primary amines with 1,3-diketones promoted by 30% aqueous H2O2 has been developed. It provides an inexpensive, regioselective, and efficient approach to 1H-pyrrol-3(2H)-ones with high yields from the simple and readily available starting materials in one pot via multicomponent tandem cyclization reactions and C-C cleavage under very mild and environmentally friendly reaction conditions.
- Sun, Xi,Li, Pinhua,Zhang, Xiuli,Wang, Lei
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supporting information
p. 2126 - 2129
(2014/05/06)
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- Direct route to 1,3-diketones by palladium-catalyzed carbonylative coupling of aryl halides with acetylacetone
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Man up your magnesium! By employing a MgCl2/Et3N system, aryl diketones can be generated from the Pd-catalyzed carbonylative α-arylation of acetylacetone with aryl bromides (see scheme). The method is ideal for the introduction of carbon isotopes into more complex structures, since only stoichiometric amounts of carbon monoxide are employed. Copyright
- Korsager, Signe,Nielsen, Dennis U.,Taaning, Rolf H.,Lindhardt, Anders T.,Skrydstrup, Troels
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supporting information
p. 17687 - 17691
(2014/01/17)
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- Palladium-catalysed carbonylative α-arylation of acetone and acetophenones to 1,3-diketones
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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
- Schranck, Johannes,Tlili, Anis,Alsabeh, Pamela G.,Neumann, Helfried,Stradiotto, Mark,Beller, Matthias
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supporting information
p. 12624 - 12628
(2013/10/01)
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- Highly atom-efficient oxidation of electron-deficient internal olefins to ketones using a palladium catalyst
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A 100 % atom-efficient synthesis of ketones from electron-deficient internal olefins was achieved using O2 as a "green" oxidant (see scheme, DMA=N,N-dimethylacetamide, EWG=electron-withdrawing group). Various electron-deficient olefins were oxidized to the corresponding ketones with over 99 % selectivity and without the formation of olefin isomers or their oxidized products. Copyright
- Mitsudome, Takato,Yoshida, Syuhei,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 5961 - 5964
(2013/06/27)
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- Tandem reactions leading to benzo[c]chromen-6-ones and 3-substituted isocoumarins
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A simple and convenient protocol for the synthesis of benzo[c]chromen-6- ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates withcyclohexane-1,3-diones or acyclic 1,3-diones is developed. This strategy can also be extended to the one-pot synthesis of isoquinolin-1(2H)-one and 3,4-dihydrophenanthridine-1,6(2H,5H)-dione. A simple and convenient protocol for the synthesis of benzo[c]chromen-6-ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates with cyclohexane-1,3-dione or acyclic 1,3-dione has been developed. This strategy can also be extended to the one-pot synthesis of isoquionlin-1(2H)-one and 3,4-dihydrophenanthridine-1,6-(2H,5H)-dione. Copyright
- Fan, Xuesen,He, Yan,Cui, Liangyan,Guo, Shenghai,Wang, Jianji,Zhang, Xinying
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supporting information; experimental part
p. 673 - 677
(2012/03/10)
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- NEW PYRAZOLE DERIVATIVES HAVING CRTH2 ANTAGONISTIC BEHAVIOUR
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 51
(2012/06/15)
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- New pyrazole derivatives having CRTh2 antagonistic behaviour
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 32
(2012/06/05)
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- Enantioselective synthesis of optically pure β-amino ketones and γ-aryl amines by Rh-catalyzed asymmetric hydrogenation
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A series of optically pure β-amino ketones have been synthesized in high enantioselectivities (ee > 99%) by Rh-DuanPhos-catalyzed asymmetric hydrogenation of readily prepared β-keto enamides. Further reduction of these β-amino ketones with hydrogen and Pd/C leads to the formation of a variety of protected enantiomerically pure γ-aryl amines (ee > 99%), which are key building blocks in many bioactive molecules.
- Geng, Huiling,Huang, Kexuan,Sun, Tian,Li, Wei,Zhang, Xiaowei,Zhou, Le,Wu, Wenjun,Zhang, Xumu
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supporting information; experimental part
p. 332 - 334
(2011/03/19)
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- Syntheses, characterization and antimicrobial evaluation of some 1, 3, 5-trisubustituted pyrazole derivatives
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A series of 1, 3, 5-trisubustituted pyrazole derivatives were synthesized and screened for antimicrobial activity. The compounds (2j-o) were evaluated against two gram-positive and two gram-negative bacteria and one fungus, at concentrations of 10 μg/mL a
- Gautam, Vertika,Chawla, Viney,Sonar, Pankaj K.,Saraf, Shailendra K.
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experimental part
p. 1190 - 1195
(2011/12/05)
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- Derivatives of N-[(1,5-diphenyl-1H-pyrazol-3-yl)methyl]sulfonamide, their preparation and their application in therapeutics
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The present invention relates to compounds corresponding to the formula (I): In which R1, R2, R3, R4 and R5 are as described herein. The invention also relates to the method of preparation of said compounds and their application in therapeutics.
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Page/Page column 18
(2008/06/13)
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- Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase
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Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
- Hollick, Jonathan J.,Rigoreau, Laurent J. M.,Cano-Soumillac, Celine,Cockcroft, Xiaoling,Curtin, Nicola J.,Frigerio, Mark,Golding, Bernard T.,Guiard, Sophie,Hardcastle, Ian R.,Hickson, Ian,Hummersone, Marc G.,Menear, Keith A.,Martin, Niall M. B.,Matthews, Ian,Newell, David R.,Ord, Rachel,Richardson, Caroline J.,Smith, Graeme C. M.,Griffin, Roger J.
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p. 1958 - 1972
(2008/02/02)
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- NOVEL DUAL ACTION RECEPTORS ANTAGONISTS (DARA) AT THE AT1 AND ETA RECEPTORS
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The present invention relates to new compounds of the formula [Chemical formula should be inserted here. Please see paper copy] wherein R1, R2, R3, and R31 are as specified herein. The invention also relates to a method for preparation thereof, as well as combinations of the new compounds with previously known agents. The invention also relates to the use of the above-mentioned compounds and combinations for the preparation of a medicament for treating hypertension of different kinds, alleviating organ damage of different kinds, treating or preventing diabetic nephropathy, treating endothelin and angiotensin mediated disorders, and treating prostate cancer.
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Page/Page column 308
(2010/11/28)
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- Proline-catalyzed aldol reactions of acyl cyanides with acetone: An efficient and convenient synthesis of 1,3-diketones
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The aldol-type addition of acetone towards (un)substituted benzoyl, heteroarylcarbonyl or α,β-unsaturated acyl cyanides was efficiently catalyzed by l-proline (30 mol %) to give 2-hydroxy-4-oxo-2-substituted pentanenitriles. Upon the treatment with sodium hydroxide, the adducts transformed to 1,3-diketones in good-to-excellent yield, furnishing an efficient and convenient method for the regioselective synthesis of 1,3-diketones.
- Shen, Zongxuan,Li, Bin,Wang, Lu,Zhang, Yawen
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p. 8785 - 8788
(2007/10/03)
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- Evaluation of TCS/ZnCl2 with acetic anhydride as an acetylating reagent for methylene ketones
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A new route for the preparation of β-diketones which have applications in organic synthesis by the reaction of methylene ketones, acetic anhydride, TCS and ZnCl2 in the solvent methylene chloride at room temperature produces the corresponding β-diketones in excellent yield. Copyright Taylor & Francis Inc.
- Elmorsy, Saad S.,Badawy, Doria S.,Khatab, Tamer K.
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p. 109 - 116
(2007/10/03)
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- Substituted oxazoles and thiazoles derivatives as hPPARγ and hPPARα activators
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The present invention discloses compounds of formula (I), and tautomeric forms, pharmaceutically acceptable salts, or solvates thereof. Preferably, the compounds of the invention are dual activators of hPPARγ and hPPAR{acute over (α)}.
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- 1-sulfonyl-3-phenylpyrazoles and their use as herbicides and for desiccating or defoliating plants
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PCT No. PCT/EP97/04911 Sec. 371 Date Mar. 17, 1999 Sec. 102(e) Date Mar. 17, 1999 PCT Filed Sep. 9, 1997 PCT Pub. No. WO98/12182 PCT Pub. Date Mar. 26, 1998The present invention relates to novel 1-sulfonyl-3-phenylpyrazoles of the formula I and agricultur
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- 13C NMR Spectroscopic Study of the Tautomeric Equilibrium in p-Phenyl Substituted Benzoylacetones
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Solution 13C NMR chemical shifts are reported for a series of p-phenyl substituted benzoylacetones which undergo a fast, intramolecular proton-transfer reaction between both possible enol tautomers.This information, together with 13C NMR spectroscopic data for related non-exchanging model compounds, allows the study of substituent-induced equilibrium shifts.The results show a systematic trend: electron-withdrawing para groups shift the equilibrium towards the methyl keto form.
- Cravero, Raquel M.,Gonzalez-Sierra, Manuel,Olivieri, Alejandro C.
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p. 1067 - 1071
(2007/10/02)
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