• Title/Summary/Keyword: Aldehyde condensation

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Studies of Porphyrin Synthesis through 3+1 Condensation

  • Lee, Chang Hui;Park, Ju Yeon;Kim, Han Je
    • Bulletin of the Korean Chemical Society
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    • v.21 no.1
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    • pp.97-100
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    • 2000
  • Acid-catalyzed porphyrin formation from meso-aryltripyrromethanes and $25-bis({\alpha}$, - hydroxyl - $\alpha$ -phenyl) methylfuran is studied. The condensation resulted in selective scrambling of tripyrromethanes when the condensation was carried out with catalytic amounts of $BF_3$ in methylene chloride. But the reaction carried out with p-TsOH or $BEt_3$ catalysts in the presence of $NH_4Cl$ in acetonitrile, single porphyrin product was isolated without scrambling of starting tripyrromethane. The yields of porphyrin in these studies were somewhat lower than those of 2+2 condensations or aldehyde-pyrrole condensations.

The Effect of pH on the Condensation Reaction of Benzaldehyde and Semicarbazide (Benzaldehyde와 Semicarbazide의 결합에 미치는 pH치의 영향)

  • 이길상;김인자
    • YAKHAK HOEJI
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    • v.6 no.1
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    • pp.5-7
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    • 1962
  • Like the condensation reaction of general aldehyde, that of benzaldehyde with semicarbazide also depends upon the concentration of carbonium ion that is produced by hydrogen ion. The lower pH value is the facility of the formation of carbonium ion in the condensation reaction, while the reactivity of semicarbazide as a reactant is reduced. In this paper, therefore we want to find out the optimum pH value in the condensation reaction of benzaldehyde with semicarbazide. This optimum pH value was determined by using the simple paper-chromatographic method. According to the result of this experiment, the condensation reaction between benzaldehyde and semicarbazide reacts with its highest point at 3.5pH value. It seems clear that at this point the benzaldehyde acquires the most suitable amount of carbonium ion for the condensation reaction with semicarbazide, and the semicarbazide also has the optimum reactivity.

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Silica Gel Promoted Mild, Efficient and Inexpensive Protocol for the Preparation of 3,4-dihydropyrano[c]chromenes (Silica Gel을 이용한 효율적인 3,4-dihydropyrano[c]chromenes의 합성)

  • Prasanna, T.S.R.;Raju, K. Mohana
    • Journal of the Korean Chemical Society
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    • v.55 no.4
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    • pp.662-665
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    • 2011
  • Highly efficient, three-component condensation of aromatic aldehyde, malononitrile and 4-hydroxycoumarin promoted by neat silica gel at room temperature is described. The method offers an excellent alternative to the synthesis of 3,4-dihydropyrano[c]chromenes. The reactions are fast and clean, and the products are obtained with good yield and purity.

Long Chain Dicationic Phase Transfer Catalysts in the Condensation Reactions of Aromatic Aldehydes in Water Under Ultrasonic Effect

  • Esen, Ilker;Yolacan, Cigdem;Aydogan, Feray
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2289-2292
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    • 2010
  • Long chain dicationic ammonium salts were used successfully as phase transfer catalyst in the condensation reactions of aromatic aldehydes in water under ultrasonic irradiation for the first time. The quaternary salt having longer distance between the cation centers was more effective than the mono- and dicationic ones having short chain.

Indium Modified Mesoporous Zeolite AlMCM-41 as a Heterogeneous Catalyst for the Knoevenagel Condensation Reaction

  • Katkar, Santosh S.;Lande, Machhindra K.;Arbad, Balasaheb R.;Rathod, Sandip B.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1301-1304
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    • 2010
  • The Indium modified mesoporous zeolite AlMCM-41 were synthesized by hydrothermal method and characterized by powder X-ray diffraction (XRD), fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy with energy dispersive spectroscopy (SEM-EDS) techniques. The Knoevenagel condensation of aldehyde with malononitrile or ethyl cyanoacetate was carried out at reflux condition in ethanol by using heterogeneous In/AlMCM-41 catalyst. This method is fast, efficient, easy work-up and eco-friendly to afford the corresponding Knoevenagel adducts. The catalyst was recovered and reused for several cycles with consistent activity.

Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates

  • Damodar, Kongara;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3618-3622
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    • 2014
  • Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, ${\alpha}$-aminophosphonate was efficiently employed in this reaction. ${\alpha}$-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.

Application of Microwave Activation Techniques to the N-Alkenyl Protection of Lactams

  • Kim, Ki-Won;Ahn, Hee-Sook;Lee, Ho-Joon;Song, Suk-Jin;Kim, Chung-Gi;Kwon, Tae-Woo
    • Bulletin of the Korean Chemical Society
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    • v.27 no.2
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    • pp.286-290
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    • 2006
  • Rapid and facile syntheses of N-alkenyl lactam series via condensation between lactams and a variety of aldehydes such as n-propanal, isobutanal, n-butanal, n-hexanal, n-octanal and phenylacetaldehyde were studied under microwave or conventional heating. Various solid catalysts and solvents were examined to maximize the yields of condensation reactions.

Synthesis of Novel 2'(β)-Methyl-5'-deoxyapiose Nucleoside Phosphonic Acid Analogues as Antiviral Agents

  • Hong, Joon Hee
    • Journal of Integrative Natural Science
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    • v.8 no.1
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    • pp.48-55
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    • 2015
  • Novel 2'(${\beta}$)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbr${\ddot{u}}$ggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydrolysis of phosphonates gave the nucleoside phosphonic acid analogue 17 and 19. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1. The adenine analogue 19 exhibited weak in vitro activities against HIV-1.

Silica Supported Ammonium Acetate: An Efficient and Recyclable Heterogeneous Catalyst for Knoevenagel Condensation between Adehydes or Ketones and Active Methylene Group in Liquid Phase

  • Gupta, Raman;Gupta, Monika;Paul, Satya;Gupta, Rajive
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2419-2421
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    • 2009
  • A simple and efficient method has been developed for Knoevenagel condensation between aldehydes or ketones and active methylene group by stirring in methylene chloride at 60 ${^{\circ}C}$ under heterogeneous conditions using silica supported ammonium acetate. The products are obtained in excellent yields and are in a state of high purity. The structures of the products were confirmed by IR, $^1H$ NMR and mass spectral data and comparison with authentic samples available commercially.

Synthesis, Characterization, Absorbance, Fluorescence and Non Linear Optical Properties of Some Donor Acceptor Chromophores

  • Asiri, Abdullah M.;Khan, Salman A.;Al-Amoudi, Muhammed S.;Alamry, Kalid A.
    • Bulletin of the Korean Chemical Society
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    • v.33 no.6
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    • pp.1900-1906
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    • 2012
  • Three carbazole chromophores featuring dicyano, cyano, ethyl acetate and dimethyl acetate groups as an acceptor moiety with a ${\pi}$-conjugated spacer and $N$-methyl dibenzo[$b$]pyrole as donor were synthesized by Knovenagel condensation and characterized by IR, $^1HNMR$, $^{13}CNMR$, UV-vis, fluorescence spectroscopy, electrochemistry and theoretical B3LYP/6-$311G^*$ level whilst NLO properties and spectroscopic quantities were calculated. Calculations showed remarkable trend with HOMO located on the donor moiety and LUMO on the acceptors dicyano methylene, cyano, ethyl acetate methylene and dimethyl acetate methylene. In agreement with the calculations, solvatochromic, behavior intramolecular charge transfer band was observed in the visible region.