• Title/Summary/Keyword: Michael products

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Studies on Synthesis and Heterocyclisation Reactions of Michael Products and Formation of New 1, 4-Thiazine Quinoxaline Derivatives

  • Mahgoub, S.A.
    • Archives of Pharmacal Research
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    • v.13 no.4
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    • pp.319-324
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    • 1990
  • Synthesis of $\alpha$-piperidino and $\alpha$-morphelino styryl quinoxalinone 2f, 2g respectively by facile one step method is reported. The Michael adducts (3a-d) obtained by the interaction of 2-styryl-2 (1H) quinoxalinone (2) and ethylacetoacetate have been treated with resorcino and hydroxylamine separately. With resorcinol the chromones (4) are obtained whereas with ydroxylamine isoxazoles (6) are the products. Michael addition of acetylacetone to 2 leads to 3-[1'-aryl-2'-(2'-hydroxy-3'-quinoxalinyl)ethyl]-2, 4-pentanediones (5) which undergo cyclisation with hydroxylamine to give isoxazoles (7). Addition of thiopenol and thioglycolic acid to 2 gives 3-$\alpha$[$\beta$-(phenyl)-$\beta$-(plenylthio)]ethyl-2(1H)-quinoxalinone (8) and 3-$\alpha$-[$\beta$-phenyl)-$\beta$-(hydroxycarbonylmethylithio)]-ethyl-2(1H)-qui noxalinone (9) respectively. 2-Bromomethyl-2(1H)-quinoxalinone (1b) reacts with thioglycolic acid to gives S-[2 (1H)-oxoquionoxaline-3-yl-methyl] mercaptoacetic acid (10) which on cyclisation with acetic anhydride/pyridine affords 1, 2, 5, 6-tetrahydro [1, 4]thiazino[4, 3-a] quinoxaline-1, 6-dione (11).

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Synthesis of Novel Ester Quaternary Ammonium Cationic Surfactants via Michael Addition Reaction (Michael Addition Reaction을 이용한 신규 Ester Quaternary Ammonium Salt 양이온 계면활성제의 합성)

  • Kang, Eun-kyung;Jung, Seon Hwa;Jung, GaYoung;Lee, Byung Min
    • Journal of the Korean Applied Science and Technology
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    • v.34 no.1
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    • pp.142-151
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    • 2017
  • Cationic surfactants have a bactericidal effect and the study for effective development of them became important parts in the industry. There have been increasing researches that focus on the development of products having not only outstanding features but also safety and biodegradability. In this work, novel ester-type cationic surfactants were obtained via Michael addition reaction. Intermediates were quantitatively prepared by the Michael addition reaction between alkyl acrylate and amine compounds under mild conditions without solvent and catalyst. The intermediates were quaternized with dimethyl sulfate. HQ21 with two hydrophobic groups and a hydrophilic group and HQ22 with two hydrophobic groups and two hydrophilic groups were obtained. The structures of the products were characterized by 1H-NMR, HR-MS and FT-IR and biodegradability of the products were tested.

Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α,β-Unsaturated Carbonyl Compounds

  • Baik, Woon-Phil;Yoon, Cheol-Hoon;Koo, Sang-Ho;Kim, Ha-Kwon;Kim, Ji-Han;Kim, Jeong-Ryul;Hong, Soo-Dong
    • Bulletin of the Korean Chemical Society
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    • v.25 no.4
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    • pp.491-500
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    • 2004
  • The Lewis acid-catalyzed reactions of anthrone with a variety of ethylenic substrates under various conditions have been studied. It has been observed that depending on kinds of ethylenic substrates and catalysts, products were varied. In particular, the $ZnCl_2$-catalyzed reaction of anthrone with ${\alpha},{\beta}$ -unsaturated ester gave bridged compounds 3 (Diels-Alder adduct type) and mono-Michael adduct 4 exclusively, while the base-catalyzed reaction gave 10,10-bis-Michael adduct as a major product independent of the amount of ethylenic substrate and base. Bridged compounds 3 were easily converted to the corresponding mono-Michael adduct 4 by a catalytic amount of base. Further Michael reaction of mono-Michael adducts with different ethylenic substrates in the presence of a catalytic amount of alkoxide gave unsymmetrical 10,10-bis Michael adducts in good or moderate yields.

Platinum-Catalyzed Reductive Aldol and Michael Reactions

  • Lee, Ha-Rim;Jang, Min-Soo;Song, Young-Jin;Jang, Hye-Young
    • Bulletin of the Korean Chemical Society
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    • v.30 no.2
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    • pp.327-333
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    • 2009
  • For the Pt-catalyzed nucleophilic addition of enones, Pt complexes were employed in the presence of various phosphine ligands and $H_2\;(or\;Et_3SiH),$ affording inter- and intra-molecular coupling products in good to modest yield. Depending on reaction protocols, different phosphine ligands were required to optimize the conditions. In the aldol reaction, the Pt catalyst involving $P(2,4,6-(OMe)_3C_6H_2)3\;or\;P(p-OMeC_6H_4)_3$ was chosen. Michael reaction proceeds in good yields in the presence of $P(p-CF_3C_6H_4)_3$. Regarding the activity of the reductants, $H_2$ exhibited superior activity to $Et_3SiH$, resulting in a shorter reaction time and higher yield in the aldol and Michael reaction. In light of the deuterium labeling studies, the catalytic cycle including the hydrometalation of the enones by the platinum hydride species was proposed.

Identification of Alkylation-Sensitive Target Chaperone Proteins and Their Reactivity with Natural Products Containing Michael Acceptor

  • Liu, Xi-Wen;Sok, Dai-Eun
    • Archives of Pharmacal Research
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    • v.26 no.12
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    • pp.1047-1054
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    • 2003
  • Molecular chaperones have a crucial role in the folding of nascent polypeptides in endoplasmic reticulum. Some of them are known to be sensitive to the modification by electrophilic metabolites of organic pro-toxicants. In order to identify chaperone proteins sensitive to alkyators, ER extract was subjected to alkylation by 4-acetamido-4 -maleimidyl-stilbene-2,2 -disulfonate (AMS), and subsequent SDS-PAGE analyses. Protein spots, with molecular mass of 160, 100, 57 and 36 kDa, were found to be sensitive to AMS alkylation, and one abundant chaperon protein was identified to be protein disulfide isomerase (PDI) in comparison with the purified PDI. To see the reactivity of PDI with cysteine alkylators, the reduced form ($PDI_{red}$) of PDI was incubated with various alkylators containing Michael acceptor structure for 30 min at $38^{\circ}C$ at pH 6.3, and the remaining activity was determined by the insulin reduction assay. Iodoacetamide or N-ethylmaleimide at 0.1 mM remarkably inactivated $PDI_{red}$ with N-ethylmaleimide being more potent than iodoacetamide. A partial inactivation of $PDI_{oxid}$ was expressed by iodoacetamide, but not N-ethylmaleimide (NEM) at pH 6.3. Of Michael acceptor compounds tested, 1,4-benzoquinone ($IC_{50}, 15 \mu$ M) was the most potent, followed by 4-hydroxy-2-nonenal and 1,4-naphthoquinone. In contrast, 1,2-naphthoquinone, devoid of a remarkable inactivation action, was effective to cause the oxidative conversion of $PDI_{red}$ to $PDI_{oxid}$. Thus, the action of Michael acceptor compounds differed greatly depending on their structure. Based on these, it is proposed that POI, one of chaperone proteins in ER, could be susceptible to endogenous or xenobiotic Michael acceptor compounds in vivo system.

Full-Color Phosphorescent OLEDs: Maximizing Performance Today for Small-Area Portable Products and Tomorrow for TVs

  • Brown, Julie J.;Adamovich, Vadim.I.;Ma, Bin;D’Andrade, Brian;Kwong, Raymond C.;Weaver, Michael S.
    • 한국정보디스플레이학회:학술대회논문집
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    • 2007.08a
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    • pp.427-430
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    • 2007
  • Phosphorescent OLED technology is a core technology driver for OLED display and lighting products due to the inherent and demonstrated efficiency advantages. Here we present recent results in our continued advancements of PHOLED power efficiency and operational stability with focus on narrowing emission line-width, reducing voltage, and overall design for maximizing device lifetime.

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Advances in E Ink Electronic Paper Display Technology and Applications

  • McCreary, Michael D.
    • 한국정보디스플레이학회:학술대회논문집
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    • 2009.10a
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    • pp.497-497
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    • 2009
  • The acceptance of electrophoretic display technology as an important alternative to both paper publishing and conventional display readers has now been proven by both the diversity and quantity of new products on the market. The current E Ink display performance as well as the recent advances in this technology will be discussed.

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SELECTIVE REDUCTION OF ACTIVE METAL CHLORIDES FROM MOLTEN LiCl-KCl USING LITHIUM DRAWDOWN

  • Simpson, Michael F.;Yoo, Tae-Sic;Labrier, Daniel;Lineberry, Michael;Shaltry, Michael;Phongikaroon, Supathorn
    • Nuclear Engineering and Technology
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    • v.44 no.7
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    • pp.767-772
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    • 2012
  • In support of optimizing electrorefining technology for treating spent nuclear fuel, lithium drawdown has been investigated for separating actinides from molten salt electrolyte. Drawdown reaction selectivity is a major issue that requires investigation, since the goal is to remove actinides while leaving the fission products and other components in the salt. A series of lithium drawdown tests with surrogate fission product chlorides was run to obtain selectivity data with non-radioactive salts, develop a predictive model, and draw conclusions about the viability of using this process with actinide-loaded salt. Results of tests with CsCl, $LaCl_3$, $CeCl_3$, and $NdCl_3$ are reported here. Equilibrium was typically achieved in less than 10 hours of contact between lithium metal and molten salt under well-stirred conditions. Maintaining low oxygen and water impurity concentrations (<10 ppm) in the atmosphere was observed to be critical to minimize side reactions and maintain stable salt compositions. An equilibrium model has been formulated and fit to the experimental data. Good fits to the data were achieved. Based on analysis and results obtained to date, it is concluded that clean separation between minor actinides and lanthanides will be difficult to achieve using lithium drawdown.

Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

  • Guo, Hui;Zhuang, Yu Wei;Cao, Jian;Zhang, Guo Bao
    • Bulletin of the Korean Chemical Society
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    • v.34 no.9
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    • pp.2594-2596
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    • 2013
  • Highly chemo- and regioselective reaction of hydroxybenzenes with ${\alpha},{\beta}$-unsaturated compounds in acidic ionic liquid l-butyl-3-methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.