• Title/Summary/Keyword: Knoevenagel reaction

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The Knoevenagel Reaction of Malononitrile with Acetylacetone: New Route of Pyrazole, Pyrazolo[2,3-C]pyridine, Benzene, Pyridazine and Benzo[C]pyridazine Derivatives

  • Mohareb, Rafat Milad
    • Archives of Pharmacal Research
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    • v.14 no.4
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    • pp.379-384
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    • 1991
  • The Knoevenagal reaction of malononitrile and acetylacetone gave the acyclic product 3 which was separated in a good yield and identified. The reactivity of 3 towards some chemical reagents is studied. Thus, the reaction of 3 with aromatic aldehydes, hydrazines and cyanomethylene derivatives gave products 6-12. Reaction of 3 with benzenediazonium chloride gave the primidine derivative 14.

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Synthesis and Potent Anti-leukemic Activity of Novel 5'-Norcarbocyclic C-nucleoside Phosphonic Acids

  • Kim, Seyeon;Kim, Eunae;Oh, Chang-Hyun;Yoo, Kyung Ho;Hong, Joon Hee
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3502-3508
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    • 2014
  • The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.

Antifungal Activities of Biorelevant Complexes of Copper(II) with Biosensitive Macrocyclic Ligands

  • Raman N.;Joseph J.;Velan A. Senthil Kumara;Pothiraj C.
    • Mycobiology
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    • v.34 no.4
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    • pp.214-218
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    • 2006
  • Four copper(II) complexes have been prepared using macrocyclic ligands. The macrocyclic ligands have been synthesized by the condensation reaction of diethyl phthalate with Schiff bases derived from o-phenylene diamine and Knoevenagel condensed ${\beta}-ketoanilides$ (obtained by the condensation of acetoacetanilide and substituted benzaldehydes). The ligands and copper complexes have been characterized on the basis of Microanalytical, Mass, UV-Vis., IR and CV spectral studies, as well as conductivity data. On the basis of spectral studies, a square-planar geometry for the copper complexes has been proposed. The in vitro antifungal activities of the compounds were tested against fungi such as Aspergillus niger, Rhizopus stolonifer, Aspergillus flavus, Rhizoctonia bataicola and Candida albicans. All the synthesized copper complexes showed stronger antifungal activities than free ligands. The minimum inhibitory concentrations (MIC) of the copper complexes were found in the range of $8{\sim}28\;{\mu}g/ml$. These compounds represent a novel class of metal-based antifungal agents which provide opportunities for a large number of synthetic variations for modulation of the activities.

Preparation and Thermal Properties of Aliphatic Network Polyester-Silica Composites (지방족 가교 폴리에스테르-실리카 복합재료의 제조 및 열적특성)

  • Oh, Chang-Jin;Park, Su-Dong;Han, Dong-Cheul;Kwak, Gi-Seop
    • Polymer(Korea)
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    • v.34 no.5
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    • pp.424-429
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    • 2010
  • The hybrid composites of aliphatic polyester-silica were prepared via a sol-gel reaction and their potential application using as a buffer coating layer in the thermoelectric device were investigated. When aliphatic polyesters were thermally treated at a high temperature of $240^{\circ}C$, the polymer showed an increases in thermal degradation temperature by $30{\sim}90^{\circ}C$ according to the thermal treatment time. The polyester-silica composites showed an increases in thermal degradation temperature by $30{\sim}50^{\circ}C$ according to the content of the added silica. Polyester-silica composite showed neither discoloration nor change in optical properties because Knoevenagel condensation reaction was hindered by silica structure. The thermal conductivity of the composites increased linearly according to the content of added silica.

Synthesis of DCM Classes Having p-Substituted Aminostyryl Groups for Red-Emitting Materials (각종 p-치환아미노스티릴기를 갖는 적색발광재료용 DCM류의 합성)

  • Chung, Pyung Jin;Sung, Jin Hee
    • Applied Chemistry for Engineering
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    • v.17 no.6
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    • pp.609-613
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    • 2006
  • 4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM) derivatives were synthesized by Knoevenagel condensation. They are red-emitting materials for OLED (Organic Light-Emitting Diode) composed of electron donor of aminostyryl groups and electron acceptor of two cyano(nitrile)groups in a conjugated structure. The structural properties of reaction products were analyzed by FT-IR and $^1H-NMR$ spectroscopy. The thermal stabilities and reactivities were measured by melting points and yields. The UV-visible and PL properties can be determined by exitation and emission spectra, respectively.

Microwave-Assisted Solvent and Catalyst Free Synthesis of 2H-Pyrans

  • Edayadulla, Naushad;Lee, Yong Rok
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.2963-2967
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    • 2013
  • This paper describes a simple and efficient method involving domino Knovenegal/$6{\pi}$ electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.

Synthesis and Characterization of New Push-Pull Chromophores Containing BF2-Azopyrrole Derivatives

  • Ko, HayeMin
    • Journal of the Korean Chemical Society
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    • v.60 no.1
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    • pp.21-27
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    • 2016
  • Novel push-pull chromophores containing 5’-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)aniline (bisDMFA) as a donor and phenylazo-methylpyrrolyl-boron difluoride (PhAPy-BF2) as an acceptor were designed and synthesized by the Knoevenagel condensation reaction for organic solar cells. Various electron withdrawing moieties were effectively introduced using 2,4-dimethyl-1H-pyrrole to afford new asymmetric BF2-azopyrrole molecules that were characterized by UV-vis spectroscopy and cyclic voltammetry measurements.

Efficient One-Pot Synthesis of Acridinediones by Indium(III) Triflate-Catalyzed Reactions of β-Enaminones, Aldehydes, and Cyclic 1,3-Dicarbonyls

  • To, Quang Huy;Lee, Yong-Rok;Kim, Sung-Hong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.4
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    • pp.1170-1176
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    • 2012
  • An efficient one-pot synthesis of acridinediones by $In(OTf)_3$-catalyzed reactions was developed starting from ${\beta}$-enaminones, aldehydes, and cyclic 1,3-diketones. The key strategies of these reactions involve domino Knoevenagel condensation/Michael addition/cyclodehydration reaction.

Immobilization of L-Lysine on Zeolite 4A as an Organic-Inorganic Composite Basic Catalyst for Synthesis of α,β-Unsaturated Carbonyl Compounds under Mild Conditions

  • Zamani, Farzad;Rezapour, Mehdi;Kianpour, Sahar
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2367-2374
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    • 2013
  • Lysine (Lys) immobilized on zeolite 4A was prepared by a simple adsorption method. The physical and chemical properties of Lys/zeolite 4A were investigated by X-ray diffraction (XRD), FT-IR, Brunauer-Emmett-Teller (BET), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and UV-vis. The obtained organic-inorganic composite was effectively employed as a heterogeneous basic catalyst for synthesis of ${\alpha},{\beta}$-unsaturated carbonyl compounds. No by-product formation, high yields, short reaction times, mild reaction conditions, operational simplicity with reusability of the catalyst are the salient features of the present catalyst.

New Strategy for the Synthesis of 5-Aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones and Their Sulfur Analogues

  • Jalilzadeh, Mohammad;Pesyan, Nader Noroozi
    • Bulletin of the Korean Chemical Society
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    • v.32 no.9
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    • pp.3382-3388
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    • 2011
  • Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and aldehydes in the presence of L-(+)-tartaric acid afforded a new route for the synthesis of stable heterocyclic 5-aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones which is a dimeric form of barbiturate (uracil and thiouracil derivative). In the reaction of 1,3-diethyl thiobarbituric acid (DETBA) the Knoevenagel condensation and then Michael adducts were obtained under the same condition. Structure elucidation is carried out by $^1H$ NMR, $^{13}C$ NMR, FT-IR and Mass analyses. Mechanism of the formation is discussed.