32818-79-4Relevant academic research and scientific papers
Dual photoredox/palladium-catalyzed C-H acylation of 2-arylpyridines with oxime esters
He, Bin-Qing,Gao, Yuan,Wang, Peng-Zi,Wu, Hong,Zhou, Hong-Bin,Liu, Xiao-Peng,Chen, Jia-Rong
supporting information, p. 373 - 377 (2020/09/11)
An unprecedented dual photoredox/palladium-catalyzed iminyl-radical-mediated C-C bond cleavage and directed ortho C-H acylation of 2-arylpyridines by using oxime esters is described. Oxime esters can serve as efficient acyl sources through formation of the corresponding acyl radicals by photoredox-catalyzed iminyl-radical-mediated C-C bond cleavage. This redox-neutral protocol features excellent regioselectivity, a broad substrate scope, and good functional-group tolerance with respect to both components, giving a broad range of aryl ketones with generally good yields.
Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids
Bai, Junxue,Li, Miao,Zhou, Cong,Sha, Yu,Cheng, Jiang,Sun, Jianwei,Sun, Song
supporting information, p. 9654 - 9658 (2021/12/14)
A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.
Discovery of a series of ruthenium(II) derivatives with α-dicarbonylmonoxime as novel inhibitors of cancer cells invasion and metastasis
He, Yihui,Xue, Huiying,Zhang, Wendian,Wang, Li,Xiang, Guangya,Li, Lei,Shang, Xianmei
, p. 82 - 92 (2017/05/19)
A series of novel ruthenium(II)-cymene complexes (1–9) with substituted α-dicarbonylmonoximes of general formula [Ru(η6-cymene)(L)Cl] (L?=?N,O-chelating bidentate α-dicarbonylmonoxime derivatives) have been synthesized and characterized by elemental analysis, IR, 1H NMR, 13C NMR spectroscopies, and in three cases by single crystal X-ray diffraction analysis. The most effective compound 9 displays remarkable anti-invasion and anti-metastasis properties without apparent cytotoxicity toward three different human cancer cell lines (MCF-7, Hela and HepG2). Further protein level studies suggest that the anti-metastasis activity of the complexes may result from the increasing expression of E-cadherin and reducing expression of Vimentin.
Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries
Gutiérrez, Rsuini U.,Rebollar, Araceli,Bautista, Rafael,Pelayo, Vanessa,Várgas, José Luis,Montenegro, Mabel M.,Espinoza-Hicks, Carlos,Ayala, Francisco,Bernal, Pablo M.,Carrasco, Cuauhtemoc,Zepeda, L. Gerardo,Delgado, Francisco,Tamariz, Joaquín
, p. 230 - 246 (2015/03/04)
Functionalized α-oximinoketones with β-alkoxy, β-alkyl, and β-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, α-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries.
TETRAZOLINONE COMPOUND AND USE THEREOF
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Paragraph 0912, (2015/11/16)
The compound represented by formula (1): wherein R4 and R5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R7, R8, and R9 each represents a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group, or the like; R13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.
METHODS OF PRODUCING MOLINDONE AND ITS SALTS
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Paragraph 0108; 0109, (2014/04/03)
The present invention is directed towards novel methods of synthesis of molindone, synthesis of the intermediates of molindone, and high-purity compositions of molindone. In particular, the invention relates to the methods of synthesis of molindone through the Mannich reaction.
Discovery and synthesis of tetrahydroindolone derived semicarbazones as selective Kv1.5 blockers
Wu, Shengde,Fluxe, Andrew,Janusz, John M.,Sheffer, James B.,Browning, Greg,Blass, Benjamin,Cobum, Keith,Hedges, Richard,Murawsky, Michael,Fang, Bin,Fadayel, Gina M.,Hare, Michelle,Djandjighian, Laurent
, p. 5859 - 5863 (2007/10/03)
A novel class of tetrahydroindolone-derived semicarbazones has been discovered as potent Kv1.5 blockers. In in vitro studies, several compounds exhibited very good potency for blockade of Kv1.5. Compound 8i showed good selectivity for blockade of Kv1.5 vs hERG and L-type calcium channels. In an anesthetized pig model, compounds 8i and 10c increased atrial ERP about 28%, 18%, respectively, in the right atrium without affecting ventricular ERP.
Polydentate ligand construction: Preparation of oximeimine complexes via intramolecular condensation reactions
Otter, Carl A.,Hartshorn, Richard M.
, p. 4193 - 4200 (2007/10/03)
Complexes of tridentate ligands containing oxime, imine and amine donor groups have been prepared both by complexation of the preformed ligands and by condensation reactions between added dionemonoxime ligands and coordinated amine ligands. Higher yields of the bis(tridentate) complexes result from the former method, while the latter method produces other complexes that may prove synthetically useful as well. Many of the complexes have been characterised by X-ray crystallographic techniques.
A Novel and Efficient Method for the Preparation of α-Hydroxyimino Carbonyl Compounds from α,β-Unsaturated Carbonyl Compounds with Butyl Nitrite and Phenylsilane Catalyzed by a Cobalt(II) Complex
Kato, Koji,Mukaiyama, Teruaki
, p. 2948 - 2953 (2007/10/02)
Various α,β-unsaturated carbonyl compounds, such as α,β-unsaturated esters, α,β-unsaturated ketones, α,β-unsaturated nitriles, and α,β-unsaturated amides, were directly converted to the corresponding α-hydroxyimino carbonyl compounds in high yields on treatment with butyl nitrite and phenylsilane in the presence of a catalytic amount of N,N'-bis(2-ethoxycarbonyl-3-oxobutylidene)ethylenediaminatocobalt(II) complex under mild conditions.
The Photochemistry of Aliphatic and Alicyclic α,β-Unsaturated Nitro Compounds. A Study of Double Bond Cleavage Following Intramolecular Cyclization and Nitro-Nitrite Rearrangement
Grant, Richard D.,Pinhey, John T.
, p. 1231 - 1244 (2007/10/02)
The light-induced intramolecular cyclization of α,β-unsaturated nitro compounds leading to double bond cleavage, which had previously been detected in a small number of β-nitrostyrenes and α-nitrostilbenes, has been shown to occur in a range of aliphatic and alicyclic α,β-unsaturated nitro compounds.At room temperature the reaction competes to a significant extent with the well known nitro-nitrite rearrangement in the irradiation of 1-nitro-2-phenylcyclohexene (2), 1-methyl-2-nitrocyclohexene (6), 1-methyl-2-nitrocycloheptene (11), 2-methyl-3-nitrobut-2-ene (23)and 2-nitro-3-phenylbut-2-ene (24), while it was the only reaction detected in the case of 1-methyl-2-nitrocyclooctene (12) and 1-nitrocyclooctene (19).No evidence for the cleavage reaction was found with 1-methyl-2-nitrocyclopentene (10), 1-nitrocyclohexene (17), 1-nitrocycloheptene (18) and 3-nitropent-2-ene (25).The nitrile oxides produced in the double bond cleavage reaction were trapped in a cycloaddition with methyl acrylate, yielding 3-substituted methyl 4,5-dihydroisoxazole-5-carboxylates.Irradiations of 1-methyl-2-nitrocyclohexene (6) and 1-methyl-2-nitrocycloheptene (11) in refluxing benzene afforded only the bridged ring isoxazolines (30) and (31) respectively.Syntheses of a number of nitro-olefins are also reported.
