16939-49-4Relevant academic research and scientific papers
Visible-light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes
Chen, Hua,Deng, Hongmei,Gong, Haiying,Hao, Jian,Li, Mingjie,Peng, Yi,Wan, Wen,Wang, Qian,Zhang, Yifang
supporting information, p. 7867 - 7874 (2021/09/28)
A visible light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radicalviaan SET pathway was involved.
Pt-catalyzed O-silylation of oximes by tri-substituted organosilanes
Bhatt, Shreeja V.,Bhatt, Shreya V.,Fotie, Jean
supporting information, p. 1636 - 1639 (2019/06/04)
Silylated derivatives of oximes are important intermediates in organic synthesis, and have found application in the preparation of various nitrogen containing compounds including nitriles, amines, nitrones, and hydroxylamines. An efficient method for the
A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
supporting information, p. 5879 - 5885 (2018/09/06)
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines
Wang, Haoxuan,Yang, Jeffrey C.,Buchwald, Stephen L.
supporting information, p. 8428 - 8431 (2017/07/06)
This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed ally
Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation
Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 3196 - 3201 (2017/04/21)
The efficient transformation of benzylamines into the corresponding oximes has been described by means of a chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90-98% isolated yield), while for the eleven synthesised aldoximes a further column chromatography purification was required (71-82% isolated yield). In all cases excellent selectivities were attained, offering a practical method for amine oxidation in short reaction times (1 hour). The environmental impact of the process was analysed and compared with a recently published alternative chemical synthesis, finding for this metric a good E-factor value.
Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts
Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo
supporting information, p. 5788 - 5793 (2016/11/06)
The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.
METHOD FOR PRODUCING ALDOXIME COMPOUND
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Paragraph 0027; 0035; 0037; 0039-0040, (2018/10/16)
PROBLEM TO BE SOLVED: To provide a method for producing an aldoxime compound using no expensive catalysts and reagents and also requiring no severe reaction conditions. SOLUTION: There is provided a method for producing an aldoxime compound containing a process where an aldehyde compound and an oxime compound are brought into trans oximation reaction in the presence of perchloric acid and/or the metallic salt of perchloric acid in an organic solvent and water. The metallic salt of perchloric acid is preferably ferric perchlorate, cobalt perchlorate, nickel perchlorate, zinc perchlorate, aluminum perchlorate or calcium perchlorate. Also, the organic solvent is preferably methylene chloride and/or ethylene dichloride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Electrochemical tandem synthesis of oximes from alcohols using KNO 3 as the nitrogen source, mediated by tin microspheres in aqueous medium
Zhang, Li,Chen, He,Zha, Zhenggen,Wang, Zhiyong
supporting information; experimental part, p. 6574 - 6576 (2012/07/30)
Electrochemical oximation of alcohols was realized with KNO3 as the nitrogen source mediated by tin microspheres.
NEW POLYMORPHIC FORMS OF N-[4-(TRIFLUOROMETHYL)BENZYL]-4-METHOXYBUTYRAMIDE
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Page/Page column 10, (2009/06/27)
Crystalline polymorphic forms of a compound of formula N-[4-(trifluoromethyl)benzyl]-4-methoxybutyramide are described. The two polymorphic forms, named polymorphic Form A and polymorphic Form B, can be used in the treatment of drug addiction and alcoholism and have very good stability. Methods for preparing the polymorphic forms are also described.
Potent inhibitors of lipoprotein-associated phospholipase A2: Benzaldehyde O-heterocycle-4-carbonyloxime
Jeong, Hyung Jae,Park, Yong-Dae,Park, Ho-Yong,Jeong, Il Yun,Jeong, Tae-Sook,Lee, Woo Song
, p. 5576 - 5579 (2007/10/03)
A series of multi-substituted oximes were prepared and their potencies for inhibiting lipoprotein-associated phospholipase A2 (Lp-PLA2) activity were evaluated in vitro. Among them, compounds 3a, 3b, and 3m were identified to display a micromolar potency for inhibiting Lp-PLA2 in whole human plasma and isolated human LDL. Based on these results, structure-activity relationship was studied on modification of three parts of R1, R2, and R3 to identify a potent pharmacophore for Lp-PLA2. In an attempt to introduce various functional groups at R2 and R3, we discovered that replacement of less lipophilic groups led to an increase of inhibitory activity. Among the tested oxime derivatives, cyano- and morpholino-substituted analogue 4f at R2 and R3 had the highest potency with an IC50 value of 0.05 μM in whole human plasma.
