3349-62-0Relevant academic research and scientific papers
Oximes: Metabolic activation and structure-allergenic activity relationships
Bergstr?m, Moa Andresen,Andersson, Sofia I.,Broo, Kerstin,Luthman, Kristina,Karlberg, Ann-Therese
, p. 2541 - 2550 (2008)
Metabolic activation of chemicals (prohaptens) in the skin can cause allergic contact dermatitis. We have explored structure-allergenic activity relationships for seven potential oxime prohaptens using the local lymph node assay and a GSH trapping screen
Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles
Lavernhe, Rémi,Torres-Ochoa, Rubén O.,Wang, Qian,Zhu, Jieping
supporting information, p. 24028 - 24033 (2021/10/07)
Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.
Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine
Kürti, László,Kattamuri, Padmanabha V.,Siitonen, Juha H.,Yousufuddin, Muhammed
supporting information, (2020/03/24)
O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.
Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
Zhu, Zhongzhi,Tang, Xiaodong,Cen, Jinghe,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 3767 - 3770 (2018/04/17)
A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.
Solvent-catalyzed umpolung carbon–sulfur bond-forming reactions by nucleophilic addition of thiolate and sulfinate ions to in situ–derived nitrosoalkenes in deep eutectic solvents
Dilauro, Giuseppe,Cicco, Luciana,Perna, Filippo Maria,Vitale, Paola,Capriati, Vito
, p. 617 - 623 (2017/05/24)
The low transition temperature mixture formed by lactic acid and choline chloride proved to be effective for an umpolung carbon–sulfur bond formation at the α-position of α-chloro oximes. Aliphatic, aromatic, and heteroaromatic thiolate and sulfinate ions
Convenient access to cycloalk-2-enone-derived N -sulfonyl imines
Hirner, Sebastian,Westmeier, Johannes,Gebhardt, Sandra,Müller, Christian H.,Von Zezschwitz, Paultheo
supporting information, p. 1697 - 1700 (2014/08/05)
The first synthesis of N-tosyl imines from various cyclopent-2-enones and cyclohex-2-enones was achieved by direct condensation with tosyl amide in the presence of TiCl(OEt)3 and Et3N. In addition, N-tert-butylsulfonyl imines from five- to seven-membered cycloalk-2-enones were obtained through formation of the respective oximes and subsequent Hudson reaction. These compounds are easy to handle solids and they are interesting starting materials for a variety of transformations. Georg Thieme Verlag Stuttgart New York.
Solventless rapid synthesis of oxime, semicarbazone, and phenylhydrazone derivatives from carbonyl compounds under microwave conditions
Kamakshi,Reddy, Boreddy S. R.
, p. 603 - 606 (2007/10/03)
A rapid and efficient method for the synthesis of oximes, semicarbazones, and phenylhydrazones has been reported under solventless conditions using microwave irradiation. CSIRO 2005.
Synthesis of (3R,4R)-3-Amino-4-hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin
Mueller, Alexander,Takyar, Dinesh K.,Witt, Sandra,Koenig, Wilfried A.
, p. 651 - 656 (2007/10/02)
(3R,4R)-3-Amino-4-hydroxyhexahydroazepine (2), the optically active constituent of the antifungal antibiotic ophicordin (1), was prepared in a multistep synthesis starting from D-serine.The absolute configuration was unambigously assigned by a comparison of the synthesized stereoisomer 2 with its racemate and the chiral moiety of the antibiotic ophiocordin by enantioselective gas chromatography. Key Words: 3-Amino-4-hydroxyhexahydroazepine / Cordyceps ophioglossoides / Antifungals / Antibiotics / Ophiocordin
Reaction of Nitrogen Dioxide with Alkenes and Polyunsaturated Fatty Acids: Addition and Hydrogen Abstraction Mechanisms
Pryor, William A.,Lightsey, John W.,Church, Daniel F.
, p. 6685 - 6692 (2007/10/02)
The reactions of nitrogen dioxide in a carrier gas (nitrogen, oxygen, or air) with cyclohexene and a series of mono-, di-, and trienes is reported at NO2 concentrations ranging from 70 ppm to 50percent.A complete product analysis was made with cyclohexene, and these data allow the calculation of the fraction of the NO2 that reacts by addition to the double bond or by abstraction of an allylic hydrogen.At high concentrations of NO2, addition is the predominant process, in agreement with the literature.However, below 10 000 ppm (1percent), hydrogen abstraction predominates.We suggest this is because of competition between a reversible addition and an irreversible H-abstraction step, much as is the case for the well-known bromine atom reaction system.In fact, a kinetic analysis shows that the ratios of rate constants for addition and abstraction are similar for both NO2 and the bromine atom.A less direct method (analysis of water formed) was used to estimate the addition to abstraction ratio for other alkenes and for esters of unsaturated fatty acids; these data are in agreement with the cyclohexene data.The autoxidation of unsaturated fatty acid esters initiated by NO2 also was studied, and kinetic chain lengths and autoxidizability ratios are given.
