- Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
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The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
- Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
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supporting information
p. 2498 - 2504
(2021/04/13)
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- Stereoselective construction of novel biaryl bridged seven-membered ring scaffolds via intramolecular [3 + 2] cycloaddition reactions
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A novel approach to biaryl bridged seven-membered carbocyclic scaffolds was developed by means of an intramolecular [3 + 2] cycloaddition process of in situ formed azomethine ylides from 2-cinnamoyl-2'-formyl biphenyl and diethyl aminomalonate hydrochlori
- Butt, Hafiza Marium,Wei, Shiqiang,Wang, Yue,Qu, Jingping,Wang, Baomin
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supporting information
(2021/11/24)
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- Green method for high-selectivity synthesis of chalcone compounds
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Under the condition of air, the water-soluble inorganic weak base is used as a catalyst to catalyze the hydrogen transfer reaction of the propargyl alcohol compound, so that the green synthesis of the high-trans selective chalcone compound is realized. Reaction temperature: 80 - 120 °C and reaction time 12 - 48 hours. To the technical scheme, any transition metal catalyst and ligand do not need to be used, inert gas protection is not needed, no other byproducts are generated, the atom economy 100%, green and environment friendliness are avoided, and the product is a high-selectivity (E)-type product. The reaction conditions are relatively low in requirement. Compared with the prior art, the alkali catalyst is obvious in advantages, and has a certain application prospect in the fields of organic synthesis, biochemistry, medicine and the like.
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Paragraph 0079-0082
(2021/10/02)
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- Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of o-Bromoacetophenones, Aldehydes, and Sodium Azide
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We herein describe an efficient copper-catalyzed three-component domino protocol used to prepare 2,1-benzoisoxazole-containing 1,2,3-triazoles from commercially available o-bromoacetophenones, aldehydes, and sodium azide. This domino process involves Aldol condensation, copper-catalyzed azide-chalcone oxidative cyclization, 1,2,3-triazole-assisted azidation, and denitrogenative cyclization sequences. The formed compounds could be considered as benzo[c]isoxazole-functionalized combretastatin A-4 triazole analogues, which might be potential applications in the discovery of a new anticarcinogen.
- Wang, Yuwei,Yu, Pei,Ren, Qingyun,Jia, Fengcheng,Chen, Yunfeng,Wu, Anxin
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p. 2688 - 2696
(2020/02/04)
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- Beyond the Corey–Chaykovsky Reaction: Synthesis of Unusual Cyclopropanoids via Desymmetrization and Thereof
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Desymmetrization-based protocols for the synthesis of highly functionalized indeno-spirocyclopropanes and cyclopropa-fused indanes have been established through unexpected reactions triggered by the Corey–Chaykovsky reagent. These structures were further elaborated in one step to privileged scaffolds such as fluorenones, indenones, and naphthaphenones. For instance, an acid-catalyzed transformation of indeno-spirocyclopropanes provided fluorenones via a homo-Nazarov-type cyclization, and naphthaphenones were obtained via an acid-catalyzed cyclopropane ring-opening/retro-Michael sequence.
- Patel, Kaushalendra,Mishra, Uttam K.,Mukhopadhyay, Dipto,Ramasastry
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supporting information
p. 4568 - 4571
(2019/11/03)
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- A pyrimidine derivatives and application thereof (by machine translation)
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The invention discloses a pyrimidine derivative and its application, the pyrimidine derivatives having the following -like type (I) indicated by the structure; wherein said R1 , R2 , R3 Are selected from the carbon atom number is 1 - 60 alkyl, substituted and non-substituted aromatic heterocyclic radical, and substituted and non-substituted aromatic ring in base of any one group. The invention through the pyrimidine derivatives key chemical structure and the like is improved, and the pyrimidine derivatives as material is applied to the electro-luminescent layer in the organic electroluminescent device, compared with the prior art can effectively solve the organic electroluminescent device in blue light material of poor stability, low efficiency and the like. (by machine translation)
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Paragraph 0079; 0081; 0082; 0083
(2018/07/30)
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- Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls
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The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.
- Jiang, Qing,Jia, Jing,Xu, Bin,Zhao, An,Guo, Can-Cheng
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p. 3586 - 3596
(2015/04/22)
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- Enantioselective synthesis of chiral 3-aryl-1-indanones through rhodium-catalyzed asymmetric intramolecular 1,4-addition
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Enantioselective synthesis of potentially useful chiral 3-aryl-1-indanones was achieved through a rhodium-catalyzed asymmetric intramolecular 1,4-addition of pinacolborane chalcone derivatives using extraordinary simple MonoPhos as chiral ligand under rel
- Yu, Yue-Na,Xu, Ming-Hua
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p. 2736 - 2741
(2013/05/21)
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- COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF
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Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.
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Paragraph 0029
(2013/03/26)
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- Synthesis of chalcone derivatives as potential anti-diabetic agents
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Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236 mg/dl) compared to pioglitazone and rosiglitazone (230 and 263 mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (≤ 238 mg/dl). The structure-activity relationship of the tested chalcones was studied and the findings were supported statistically.
- Hsieh, Chi-Ting,Hsieh, Tusty-Jiuan,El-Shazly, Mohamed,Chuang, Da-Wei,Tsai, Yi-Hong,Yen, Chiao-Ting,Wu, Shou-Fang,Wu, Yang-Chang,Chang, Fang-Rong
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supporting information; experimental part
p. 3912 - 3915
(2012/07/03)
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- Fused benzo[b]fluorenols: Palladium-catalyzed intramolecular dehydroaromatization and carbonyl reduction
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Benzo[b]fluorenols were prepared by a new palladium-catalyzed one-pot reaction of en-one-ynes with 3-bromoprop-1-yne through intramolecular dehydroaromatization and carbonyl reduction. Copyright
- Zhao, Quansheng,Hu, Qiong,Wen, Lei,Wu, Min,Hu, Yimin
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supporting information
p. 2113 - 2116
(2012/11/06)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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- Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction
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(Chemical Equation Presented) An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.
- Minatti, Ana,Zheng, Xiaolai,Buchwald, Stephen L.
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p. 9253 - 9258
(2008/03/13)
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- Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones
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We have developed a novel and versatile synthesis of racemic 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones. This method is especially attractive because it avoids strong acidic conditions and consequently a larger number of sensitive functional groups are accepted during synthesis compared with existing methods.
- Pueschl, Ask,Rudbeck, Hans Christian,Faldt, Andre,Confante, Allesia,Kehler, Jan
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p. 291 - 295
(2007/10/03)
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- 2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis
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A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1β from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-μM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings β to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.
- Batt,Goodman,Jones,Kerr,Mantegna,McAllister,Newton,Nurnberg,Welch,Covington
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p. 1434 - 1442
(2007/10/02)
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