- Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities
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In this study, hydroxy benzoin (1-7), benzil (8-14), and benzoin/benzil-O-β-D-glucosides (15-25) were synthesized to investigate their biological activities. An efficient method for synthesizing hydroxy benzoin compounds (1-7) was prepared from four diffe
- Yayli, Nurettin,Kili?, G?zde,Celik, Gonca,Kahriman, Nuran,Kanbolat, Seyda,Bozdeveci, Arif,Karaoglu, Sengül Alpay,Aliyazicioglu, Rezzan,Sellitepe, Hasan Erdin?,Dogan, Inci Selin,Aydin, Ali
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p. 788 - 804
(2021/07/26)
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- Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature
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We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ~2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is
- Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Sagadevan, Arunachalam
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supporting information
p. 4426 - 4432
(2020/08/10)
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- Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives
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The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines is reported. These aldimines react with Weinreb amides, ketones, or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allows for an efficient synthesis of 1,2-dicarbonyl compounds and α-hydroxy ketones.
- Schw?rzer, Kuno,Bellan, Andreas,Z?schg, Maximilian,Karaghiosoff, Konstantin,Knochel, Paul
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p. 9415 - 9418
(2019/05/10)
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- Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds
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Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.
- Kim, Seung Woo,Um, Tae-Woong,Shin, Seunghoon
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supporting information
p. 4703 - 4711
(2018/04/26)
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- β-Cyclodextrin/IBX in water: Highly facile biomimetic one pot deprotection of THP/MOM/Ac/Ts ethers and concomitant oxidative cleavage of chalcone epoxides and oxidative dehydrogenation of alcohols
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A mild and efficient one-pot deprotection of THP/MOM/Ac/Ts ethers, and concomitant oxidative cleavage of epoxides and oxidative dehydrogenation of alcohols to form β-hydroxy 1,2-diketones, 1,2,3-triketones and conjugated aromatic carbonyl systems (chalcones) using β-cyclodextrin/IBX in water has been developed. o-Iodoxybenzoic acid, a readily available hypervalent iodine(v) reagent, was found to be highly effective with β-cyclodextrin in carrying out the deprotection and subsequent transformations under an eco-friendly environment. The reaction gave moderate to excellent yields ranging from 50-99% at 60°C in 40 min to 6 h.
- Kumar, Sumit,Ahmed, Naseem
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supporting information
p. 648 - 656
(2016/02/12)
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- Direct Construction of 4-Hydroxybenzils via Para-Selective C-C Bond Coupling of Phenols and Aryl Methyl Ketones
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A highly para-selective C-C bond coupling is presented between phenols C(sp2) and aryl methyl ketones C(sp3), which enables the direct construction of 4-hydroxybenzil derivatives. This practical method exhibits a broad substrate scop
- Xiang, Jia-Chen,Cheng, Yan,Wang, Miao,Wu, Yan-Dong,Wu, An-Xin
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supporting information
p. 4360 - 4363
(2016/10/09)
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- Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring Expansion of Alkynyl Quinols
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A new and convenient strategy for the synthesis of functionalized tropone derivatives based on the gold-catalyzed oxidative ring expansion of alkynyl quinols has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation foll
- Zhao, Jidong,Liu, Jun,Xie, Xin,Li, Shi,Liu, Yuanhong
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supporting information
p. 5926 - 5929
(2015/12/11)
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- Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts
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Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.
- Jung, Michael E.,Deng, Gang
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supporting information
p. 2142 - 2145
(2014/05/06)
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- Transition metal-free oxidation of ynamides for synthesis of α-keto-imides
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Transition metal-free double oxidation of triple bonds in ynamides for synthesis of α-keto-imides is described. The successful key was combination of NIS and DMSO under atmospheric air in CPME solvent, and the reaction quickly proceeds at 0 °C within 1 h.
- Chikugo, Takuya,Yauchi, Yuta,Ide, Masataka,Iwasawa, Tetsuo
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p. 3988 - 3993
(2014/06/09)
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- Design, synthesis, and cytotoxic activities of new 2,4,5-triarylimidazoles
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A new group of 2,4,5-triarylimidazoles containing N,N-dimethylaminoethoxy or piperidinyl ethoxy group at the para position of the C-5 phenyl ring were synthesized and their cytotoxic activities were evaluated on three different breast cancer cell lines using MTT assay. The compounds contain various substituents at the para position of C-2 phenyl ring. Among the synthesized compounds, 4-(5-(4-(2-piperidin-1-yl)ethoxy)phenyl)-4-phenyl-1H-imidazol-2-yl) phenol (11e) and 1-2-(4-(2,4-diphenyl-1H-imidazol-5-yl)phenoxy)ethyl) piperidine (11h) with IC50s of less than 0.1 μM on all three cell lines were the most potent cytotoxic compounds.
- Zarghi,Arfaei,Shirazi
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p. 3897 - 3904
(2013/07/26)
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- Pyridine N-oxide mediated oxidation of diarylalkynes with palladium on carbon
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Pyridine N-oxide works as an effective oxidant of 1,2-diarylalkynes at 120 °C to form benzil derivatives under Pd/C-catalyzed solvent-free conditions, and Pd/C could be reused up to five times after simple filtration.
- Sawama, Yoshinari,Takubo, Masato,Mori, Shigeki,Monguchi, Yasunari,Sajiki, Hironao
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experimental part
p. 3361 - 3367
(2011/07/29)
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- Mild oxidation of diarylacetylenes to 1,2-diketones using oxone in trifluoroacetic acid
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A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl) benzene and 2,4¢-(ethyne-1,2-diyl) bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophenyl)methanone as the major products, respectively. Georg Thieme Verlag Stuttgart.
- Chu, Jean-Ho,Chen, Yen-Ju,Wu, Ming-Jung
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experimental part
p. 2155 - 2162
(2009/12/27)
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- DMSO-PdI2 as a powerful oxidizing couple of alkynes into benzils: one-pot synthesis of nitrogen-containing five- or six-membered heterocycles
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PdI2 in DMSO promoted the oxidation of functionalized diarylalkynes into benzil derivatives in excellent yields. This new oxidation reaction was achieved with short reaction times and low loading of palladium catalyst. This efficient catalytic
- Mousset, Céline,Provot, Olivier,Hamze, Abdallah,Bignon, Jér?me,Brion, Jean-Daniel,Alami, Mouad
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p. 4287 - 4294
(2008/09/19)
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- Microwave-assisted efficient synthesis of 1,2-diaryldiketones: a novel oxidation reaction of diarylalkynes with DMSO promoted by FeBr3
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This paper reports the oxidation of functionalized diarylalkynes with DMSO in the presence of the environmentally friendly FeBr3 catalyst. This non-toxic procedure is general and has been applied successfully under microwave irradiation leading rapidly to benzil derivatives in good yields.
- Giraud, Anne,Provot, Olivier,Peyrat, Jean-Fran?ois,Alami, Mouad,Brion, Jean-Daniel
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p. 7667 - 7673
(2007/10/03)
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- Diphenyl disulfide and sodium in NMP as an efficient protocol for in situ generation of thiophenolate anion: Selective deprotection of aryl alkyl ethers and alkyl/aryl esters under nonhydrolytic conditions
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Aryl methyl ethers, methyl esters, aryl esters, and aryl sulfonates are chemoselectively deprotected under nonhydrolytic conditions by treatment with Ph2S2 (0.6 equiv) and Na (1.6 equiv) in NMP under reflux or at 90°C. Quantitative utilization of the 'PhS' moiety as the effective nucleophilic species represents conservation of atom economy. Other solvents such as HMPA, DMPU, DMEU, and DMF afforded comparable results. Chloro, nitro, aldehyde, α,α-diketone, and α,β-unsaturated ketone functionalities remain unaffected. The deprotection was found to take place in the order aryl ester > alkyl ester > aryl alkyl ether. Substrates bearing strong electron-withdrawing groups react at a faster rate than those not having such substitution. The differences in rate of reaction has been exploited for selective deprotection for intramolecular competition. An aryl acetate/benzoate is deprotected selectively in preference to a methyl ester or aryl methyl ether. Selective deprotection of a methyl ester is observed in the presence of an aryl alkyl ether.
- Chakraborti, Asit K.,Nayak, Mrinal K.,Sharma, Lalima
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p. 1776 - 1780
(2007/10/03)
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- Demand-based thiolate anion generation under virtually neutral conditions: Influence of steric and electronic factors on chemo- and regioselective cleavage of aryl alkyl ethers
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Thiolate anions have been generated in a "demand-based" fashion under virtually neutral conditions for chemoselective deprotection of aryl alkyl ethers. Solvents play the critical role in making the reaction effective and should have high values of ε (>30), molecular polarizabilities (>10), and DN (>27) and low values of AN (>14). However, it is the combined effect of all of these physical properties that make a particular solvent effective. The reaction rates of cleavage of various aryl alkyl ethers are dependent on the steric crowding around the O-alkyl carbon and follow the order propargyl ≈ allyl ≈ benzyl > methyl > ethyl. Electron-withdrawing substituents increase the rate of ether cleavage reaction. The influence of the steric and electronic factors have been successfully exploited for selective deprotection of aryl alkyl ethers during inter- and intramolecular competitions.
- Chakraborti, Asit K.,Sharma, Lalima,Nayak, Mrinal K.
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p. 6406 - 6414
(2007/10/03)
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- Chromophoric photocrosslinking compound
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A photoactive compound that is the reaction product of an alkenyl azlactone compound and a nucleophilic aromatic ketone is described. Mer units derived from this compound can be used, for example, to crosslink via a hydrogen abstracting mechanism acrylic polymers in which they are incorporated.
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- Chemoselective aryl alkyl ether cleavage by thiophenolate anion through its in situ generation in catalytic amount
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Catalytically in sutu generated alkali metal thiophenoxide in NMP (1-melhyl-2-pyrrolidinone) chemoselectively cleaves aryl alkyl elhers in high yields.
- Nayak, Mrinal K.,Chakraborti, Asit K.
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p. 8749 - 8752
(2007/10/03)
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- New DMSO-Based Reagents in Oxidation of Double and Triple Bonds and Synthesis of 1,2-Diketones
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Preparative possibilities of oxidation of arylethenes and arylethynes using new reagents, iodine or palladium compounds in dimethylsulfoxide, in syntheses of 1,2-diketones are considered.The system PdCl2-Me2SO is shown to possess lower activity as compared to I2-Me2SO in oxidation of the double bonds, higher selectivity in oxidation of the triple bonds of diarylethynes and phenylpropyne, but more sensitive to steric effects of the substrate.
- Yusubov, M. S.,Chi, Ki Whan,Krasnokutskaya, E. A.,Vasil'eva, V. P.,Filimonov, V. D.
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p. 1503 - 1506
(2007/10/03)
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- REACTIONS OF NITRILE OXIDES WITH 2-LITHIO-1,3-DITHIANES, SYNTHESIS OF α-DIKETONES
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Nitril oxides (2) were treated with 2-lithio-1,3-dithianes (4) to give in good yields masked ketoximes (5), new synthetic tools for α-diketones.
- Yamamori, Teruo,Adachi, Ikuo
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p. 1747 - 1750
(2007/10/02)
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