4480-47-1Relevant academic research and scientific papers
Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers
De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui
supporting information, p. 20501 - 20512 (2021/12/03)
The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.
Novel synthesis method of metribuzin intermediate
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, (2020/01/25)
The invention discloses a novel synthesis method of a metribuzin intermediate, wherein the intermediate triazinone of metribuzin is produced by using pinacolone (methyl tert-butyl ketone) as an initial raw material through reaction steps of chlorination, hydrolysis, oxidation, condensation and the like. According to the invention, the reaction conditions are mild, and the total yield reaches 92.4%; hydrogen peroxide is used as an oxidizing agent for replacing sodium hypochlorite, and the oxidation reaction is carried out at a room temperature, so that the operation is convenient, and the byproduct is water so as to avoid the discharge of pollutants such as salt-containing wastewater and the like in the production process; and after the reaction is finished, the intermediate and the catalyst are subjected to chromatographic separation so as to recycle the water phase containing the catalyst.
Stereocontrolled Synthesis of 1,4-Dicarbonyl Compounds by Photochemical Organocatalytic Acyl Radical Addition to Enals
Goti, Giulio,Bieszczad, Bartosz,Vega-Pe?aloza, Alberto,Melchiorre, Paolo
supporting information, p. 1213 - 1217 (2019/01/04)
We report a visible-light-mediated organocatalytic strategy for the enantioselective acyl radical conjugate addition to enals, leading to valuable 1,4-dicarbonyl compounds. The process capitalizes upon the excited-state reactivity of 4-acyl-1,4-dihydropyridines that, upon visible-light absorption, can trigger the generation of acyl radicals. By means of a chiral amine catalyst, iminium ion activation of enals ensures a stereoselective radical trap. We also demonstrate how the combination of this acylation process with a second catalyst-controlled bond-forming event allows to selectively access the full matrix of all possible stereoisomers of the resulting 2,3-substituted 1,4-dicarbonyl products.
Method for synthesizing tetra-2,3-(5-t-tutylpyrazine)metalloporphyrin
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Paragraph 0048; 0049; 0052; 0053; 0056; 0057, (2017/07/22)
The invention relates to a method for synthesizing tetra-2,3-(5-t-tutylpyrazine)metalloporphyrin. The method comprises the following steps: using 3,3-dimethyl-2-butanone as a raw material, carrying out a selenizing reaction with selenium dioxide, and rectifying the product to obtain 3,3-dimethyl-2-oxobutryaldehyde; heating 3,3-dimethyl-2-oxobutryaldehyde obtained in the above step in the condition that 2,3-diamido-2-2-butene dinitrile, urea and metal chloride exist, and purifying the product to obtain the tetra-2,3-(5-t-tutylpyrazine)metalloporphyrin. According to the method, the tetra-2,3-(5-t-tutylpyrazine)metalloporphyrin can be obtained only through a two-step reaction of selenylation and synthesis and then through simple purification, the process is simple, and the product is controllable; the used raw materials are simple, and the cost is low; no poisonous or harmful waste product is produced in the middle process, so that the process of after-treatment is greatly reduced. The tetra-2,3-(5-t-tutylpyrazine)metalloporphyrin prepared in the invention is high in yield.
Method for preparing a triazones (by machine translation)
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Paragraph 0034; 0036, (2017/01/23)
The invention discloses a method for preparing a triazones of: the two chlorine frequency alkone in the organic solvent and in the presence of the catalyst, in the 80 °C -140 ° C reaction under 1-3 hours, then post-processed to obtain compound I, compound I in the presence of an oxidizing agent and solvent, in 0 °C -40 ° C the oxidation reaction under 1-4 hours, a solution of trimethyl pyruvic acid obtained, the trimethyl pyruvic acid solution and sulfur under catalysis of carbazide in acid , in the 70 °C -90 ° C a cyclization reaction under 2-5 hours, then post-processed to obtain the triazones. The preparation method of this invention simple step, the raw materials are easy to obtain, the cost is low, does not produce high salt waste water, more consistent with the requirements of environmental protection, is suitable for industrial production, and, ultimately, to the yield of the product and the content is relatively high. (by machine translation)
Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans
Dunn, Jonathan,Dobbs, Adrian P.
supporting information, p. 7386 - 7414 (2015/08/24)
Abstract A detailed study on the synthesis and reactions of silylmethylcyclopropanes is reported. In their simplest form, these donor-only cyclopropanes undergo Lewis acid promoted reaction to give either cis- or trans-tetrahydrofurans, with the selectivity being reaction condition-dependant. The adducts themselves are demonstrated to be an important scaffold for structural diversification. The combination of a silyl-donor group in a donor-acceptor cyclopropane with novel acceptor groups is also discussed.
One-pot three-component reactions of methyl ketones, phenols and a nucleophile: An expedient way to synthesize densely substituted benzofurans
Cheng, Cheng,Liu, Changhui,Gu, Yanlong
, p. 8009 - 8017 (2015/12/31)
Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol.
Three-component povarov reaction-heteroannulation with arynes: Synthesis of 5,6-dihydroindolo[1,2-a ]quinolines
Bunescu, Ala,Wang, Qian,Zhu, Jieping
supporting information, p. 1756 - 1759 (2014/04/17)
A reaction of 2-acyl substituted tetrahydroquinolines, prepared by Lewis acid-catalyzed three-component reaction of α-oxo aldehydes, anilines, and dienophiles, with in situ generated arynes afforded 5,6-dihydroindolo[1,2-a] quinolines in good to excellent
New procedures for preparing 2,2,3,3-tetracyanocyclopropyl ketones
Bardasov,Kayukova,Kayukov,Ershov,Nasakin
experimental part, p. 1431 - 1434 (2010/01/05)
New procedures were developed for preparing 2,2,3,3-tetracyanocyclopropyl ketones, based on reactions of substituted glyoxals with bromomalononitrile.
Synthesis and anti-protozoal activity of C2-substituted polyazamacrocycles
Reid, Caroline M.,Ebikeme, Charles,Barrett, Michael P.,Patzewitz, Eva-Maria,Mueller, Sylke,Robins, David J.,Sutherland, Andrew
, p. 2455 - 2458 (2008/09/21)
A focused library of C2-substituted-1,4,7,10-tetraazacyclododecanes was synthesised and the compounds were tested for their ability to kill trypanosome and malaria parasites. Several compounds showed significant in vitro activity and were selectively active against the parasites over human embryonic kidney cells used as a counter screen.
