313236-80-5Relevant academic research and scientific papers
Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes
Zhang, Xiong,Jones-Mensah, Ebenezer,Deobald, Jackson,Magolan, Jakob
supporting information, p. 5548 - 5551 (2019/11/19)
We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).
Domino-Fluorination-Protodefluorination Enables Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids with Styrene via Photoredox Catalysis
Zhang, Muliang,Xi, Junwei,Ruzi, Rehanguli,Li, Nan,Wu, Zhongkai,Li, Weipeng,Zhu, Chengjian
, p. 9305 - 9311 (2017/09/25)
Domino-fluorination-protodefluorination decarboxylative cross-coupling of α-keto acids with styrene has been developed via photoredox catalysis. The critical part of this strategy is the formation of the carbon-fluorine (C-F) bond by the capture of a carbon-centered radical intermediate, which will overcome side reactions during the styrene radical functionalization process. Experimental studies have provided evidence indicating a domino-fluorination-protodefluorination pathway with α-keto acid initiating the photoredox cycle. The present catalytic protocol also affords a novel approach for the construction of α,β-unsaturated ketones under mild conditions.
Phosphorous Acid Promoted Hydration-Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System
Zhou, Yongbo,Li, Zhongwen,Yang, Xiao,Chen, Xiulin,Li, Mei,Chen, Tieqiao,Yin, Shuang-Feng
, p. 231 - 237 (2016/01/12)
A simple and environmentally benign method was developed for the synthesis of chalcones in high to excellent yields by a phosphorous acid promoted alkyne-aldehyde hydration-condensation in an oil/water two-phase system. The method is the first efficient protocol for the preparation of chalcones that is mediated by a simple Bronsted acid in a two-phase system.
Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives
Evranos-Aks?z, Begüm,Baysal, Ipek,Yabano?lu-?ift?i, Samiye,Djikic, Teodora,Yelek?i, Kemal,U?ar, Gülberk,Ertan, Rahmiye
, p. 743 - 756 (2015/10/12)
A group of 3,5-diaryl-2-pyrazoline and hydrazone derivatives was prepared via the reaction of various chalcones with hydrazide compounds in ethanol. Twenty original compounds were synthesized. Ten of these original compounds have a pyrazoline structure, n
Syntheses and biological activity of chalcones-imidazole derivatives
Liu, Yu-Ting,Sun, Xiao-Ming,Yin, Da-Wei,Yuan, Fang
, p. 1037 - 1048 (2013/06/04)
A number of novel 13-membered chalcone-imidazole derivatives were prepared and have been synthesized and characterized by IR, 1H NMR, 13C NMR and elemental analysis, the results conformed well to expected structures. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Methyl on the aromatic ring of chalcones was brominated by NBS, and then the resulting mixture was reacted with imidazole to get the target compound. Several chalcones showed in vitro antibacterial activity against Gram-bacterial. The results showed that these are potential antibacterial compounds.
Solution-phase parallel synthesis of substituted chalcones and their antiparasitary activity against Giardia lamblia
Montes-Avila, Julio,Diaz-Camacho, Sylvia P.,Sicairos-Felix, Josefina,Delgado-Vargas, Francisco,Rivero
experimental part, p. 6780 - 6785 (2009/12/06)
A library of 25-membered chalcones was prepared by parallel synthesis. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Several chalcones showed in vitro antiparasitic activity against Giardia lamblia. The highest activity observed for the IC50 values were 12.72, 15.05 and 15.31 μg/mL, respectively; these are potential leads for the development of antigiardial compounds.
Synthesis of some new 1-(6-fluorobenzothiazol-2-yl)-3-(4-fluoro- phenyl)-5-arylpyrazolines and their iodine(III) mediated oxidation to corresponding pyrazoles
Aggarwal, Ranjana,Kumar, Vinod,Singh, Shiv P
, p. 1332 - 1336 (2008/09/18)
The reaction of fluorinated chalcones 2 and 6-fluorobenzothiazol-2- ylhydrazine 1 in presence of catalytic amount of glacial acetic acid in refluxing ethanol yields l-(6-fluorobenzothiazol-2-yl)-3-(4-fluorophenyl)-5- arylpyrazolines 3, which undergo facile oxidation to the corresponding pyrazoles 4 in good yield using iodobenzene diacetate (IBD). The structures of the synthesized compounds have been established on the basis of their elemental analysis, MS and 1H and 13C NMR spectroscopy.
Polarographic Investigations on α,β-Unsaturated Ketones: 1-(4'-Fluorophenyl)-3-phenyl-2-propenones
Katiyar, Sarvagya S.,Latithambica, M.
, p. 956 - 960 (2007/10/02)
The reduction of various substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones at the dropping mercury electrode has been examined.In 50percent ethanol-water buffered media fluorochalkones give two well-defined waves in acid media and three waves in neutral and alkaline media.The one-electron electroreduction in the first two steps results in the formation of dihydrochalcone, which subsequently gets further reduced to the secondary alcohol.A large variety of substituents on the benzylidene moiety of 1-(4'-fluorophenyl)-3-phenyl-2-propenone, affect the half-wave potentials according to the relation E1/2 = a + b.Substituents with a positive ? value render the reduction easier and shift the E1/2 to more positive values, whereas groups with negative ? values make the electroreduction more difficult, resulting in more negative E1/2 compared to the parent compound.A comparison of the E1/2 values of o- and p-chloro substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones shows that o-substituted derivative undergoes reduction at a more positive potential indicating a positive ortho effect for this system.
