- Electrochemical Synthesis of 2-Bromoethyl and 2-Iodoethyl Ketones from Cyclopropanols
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A simple electrochemical protocol for the preparation of 2-bromoethyl- and 2-iodoethyl ketones from cyclopropanols and magnesium halides has been developed. The reaction proceeded with exclusive regioselectivity and without epimerization of the α-stereocenter in the products. We also showed that the synthesized diastereomerically pure 2-bromoethyl ketones undergo smooth copper and nickel-catalyzed alkylation, alkenylation, and arylations reactions.
- Barysevich, Maryia V.,Aniskevich, Yauhen M.,Hurski, Alaksiej L.
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supporting information
p. 1934 - 1938
(2021/10/19)
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- Transformation of arenes into 3-arylpyrazoles and 3-arylisoxazolines with β-bromopropionyl chloride, hydrazine, and hydroxylamine
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Successive treatment of arenes with β-bromopropionyl chloride and AlCl3, followed by the reactions with hydrazines and Na2CO3, and then with MnO2 gave the corresponding 3-arylpyrazoles in one pot in good to moderate yields. The same successive treatment of arenes with β-bromopropionyl chloride and AlCl3, followed by the reactions with hydroxylamine and KF gave the corresponding 3-arylisoxazolines in one pot in good to moderate yields.
- Yamamoto, Takahiro,Togo, Hideo
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- Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones
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Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.
- An, Sejin,Moon, Da Yoon,Park, Bong Ser
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p. 6922 - 6928
(2018/10/24)
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- Novel compound capable of activating Nrf2, and pharmaceutical compositions comprising the same
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The present invention provides a novel compound which can activate Nrf2 that is a transcription factor for expression of the quinone reductase gene. Therefore the compound is effective for inhibiting apoptosis and preventing and treating brain nerve disea
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Paragraph 1069-1072
(2016/10/08)
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- Solid-supported cross-metathesis and a formal alkane metathesis for the generation of biologically relevant molecules
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Solid-phase synthetic strategies toward the generation of libraries of biologically relevant molecules were developed using olefin cross-metathesis as a key step. It is remarkably the formal alkane metathesis based on a one-pot, microwave-assisted, ruthenium-catalyzed cross-metathesis and reduction to obtain Csp3-Csp3 linkages.
- Mndez, Luciana,Mata, Ernesto G.
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- Anodic cyclization of dimethyl 2-(3-Oxo-3-arylpropyl) malonates into the corresponding dimethyl 2-aroylcyclopropane-1,1-dicarboxylates
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A variety of dimethyl 2-(3-oxo-3-arylpropyl)malonates were electrooxidized in methanol, in the presence of potassium iodide and a base or a neutral salt, to give the corresponding cyclized dimethyl 2-aroylcyclopropane-1,1- dicarboxylates in moderate to good yields. The reactions were carried out under extremely mild reaction conditions, in which the optimal amount of electrolytic current varied from 2.12-2.41 F·mol-1 depending on the substrates. The reaction presumably proceeds via a two-electron oxidation process, in which iodide ions play an important role as the electron carrier between the anode and the substrate. Georg Thieme Verlag Stuttgart. New York.
- Okimoto, Mitsuhiro,Yamamori, Haruki,Ohashi, Kousuke,Hoshi, Masayuki,Yoshida, Takashi
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p. 1568 - 1572
(2013/08/23)
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- Synthesis and Nrf2 activating ability of thiourea and vinyl sulfoxide derivatives
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Thiourea and vinyl sulfoxide derivatives were designed based on the structures of sulforaphane and gallic acid, prepared and tested for HO-1 inducing activity as a measure of Nrf2 activation, and inhibitory effect on NO production as a measure of anti-inf
- Shim, Young Sun,Hwang, Hyun Sook,Nam, Ghilsoo,Choi, Kyung Il
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p. 2317 - 2320
(2013/09/24)
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- Azido carbonyl compounds as DNA cleaving agents
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Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
- Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
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- Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade
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A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities. Georg Thieme Verlag Stuttgart - New York.
- Rueping, Magnus,Hubener, Lukas
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supporting information; experimental part
p. 1243 - 1246
(2011/07/31)
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- An efficient and general approach to β-functionalized ketones
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Figure presented The oxidation of selected anlons (N3 -, SCN-, I-, and Br-) by eeric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to β-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.
- Jingliang, Jiao,Nguyen, Larry X.,Patterson, Dennis R.,Flowers II, Robert A.
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p. 1323 - 1326
(2008/01/01)
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- EFFECT OF THE STRUCTURE OF THE REAGENTS ON THE FORMATION RATE OF ARYL VINYL KETONES IN THE REACTION OF AMINES WITH β-HALOGENOPROPIOPHENONES
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The dependence of the formation rate of aryl vinyl ketones in the reaction of ring-substituted β-halogenopropiophenones with various amines on the structure of the reagents was investigated.By analysis of the obtained data it was concluded that the process takes place by an E2 mechanism through an anion-like transition state.
- Popov, A. F.,Piskunova, Zh. P.,Matvienko, V. N.
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p. 1918 - 1921
(2007/10/02)
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