• Title/Summary/Keyword: 1,2-Diketone

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Transformation of Bicyclic Ketal Compound to 1,2-Cyclopentanediol via 1,5-Diketone

  • Jun Jong-Gab;Shin Dong Gyun;Shin Hyun Shun;Kim Sung Hoon
    • Bulletin of the Korean Chemical Society
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    • v.13 no.2
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    • pp.176-179
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    • 1992
  • New method for preparing cyclopentanediol from bicyclic ketal is described. Bicyclic ketal is cleaved to give 1,5-diketone, which is then reductively coupled intramolecularly to yield 1,2-cyclopentanediol. A solution of bicyclic ketal (1a) in methylene chloride was treated with aluminum chloride(2 eq.)-sodium iodide(l.5 eq.) at ambient temperature for 3 h to give the 1,5-diketone (2a) in 71% yield after basic work-up followed by short path column chromatography. A solution of the 1,5-diketone (2a) in THF was reacted with titanium tetrachloride(6 eq.)-Mg(Hg)(0.3 eq.) at $0^{\circ}C$ for 4 h to give the 1,2-cyclopentanediol (3a) in 75% yield after basic work-up followed by short path column chromatography.

Sensitized Near IR Luminescence of Er(Ⅲ) Ion in Lanthanide Complexes Based on Diketone Derivatives: Synthesis and Photophysical Behaviors

  • Baek, Nam-Seob;Kwak, Bong-Kyu;Kim, Yong-Hee;Kim, Hwan-Kyu
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1256-1260
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    • 2007
  • Two β-diketone derivatives bearing triphenylene (1-naphthalene-2-yl-3-triphenylen-2-yl-propane-1,3-dione (NTPD)) and naphthalene (1,3-di-naphthalene-2-yl-propane-1,3-dione (DNPD)) and their Ln(III) complexes (Ln = Er or Gd) were synthesized and their photophysical properties were investigated. The sensitized emission of Er3+ ion in Er3+-[NTPD]3(terpy) and Er3+-[DNPD]3(terpy) was observed upon excitation at absorption maximum of ligands. Their photophysical studies indicate the sensitization of Er3+ luminescence by energy transfer through the excited triplet state of β-diketone ligand. The energy transfer rate through the excited triplet state of β-diketone ligand to Er3+ ion occurs faster than that of the oxygen quenching rate.

Synthesis of Quinazoline 4-one Drvivatives from 2-Aminobenzamide(II) - Reaction with $\gamma$-Lactone and Diketone (2-Aminobenzamide로부터 Quinazoline 4-one 유도체의 합성 (II) - $\gamma$-락톤과 디케톤과의 반응)

  • 서명은
    • YAKHAK HOEJI
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    • v.30 no.5
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    • pp.203-207
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    • 1986
  • 2-Aminobenzamide reacts with not only keton radical but also carbonyl group in carboxylic acid, to form easily -N-C-N-novel ring cyclization as a result I and V. In addition, it reacts with 1, 2-cyclohexadione or benzil, whitch are both 1, 2-diketone compounds, at the both ketone radical sites to give V or VII respectively. On the reaction with dimethone, however, which has 1, 3-diketone radical, it reacted with only one carbanyl group and VI was produced. We investigated the reaction with cr-ketoester such as ethyl pyruvate and diethyl rnesoxalate. In the reaction with ethylpyruvate, amine group in 2-aminobenzamide reacted not with ketone radical but carbonyl group in ester (product VIII). On the other hand, diethyl measoxalate reacted at the ketone radical site rather than the ester site (product IX).

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Preparation and Luminescent Properties of a Novel Carbazole Functionalized Bis-β-diketone Ligand and Corresponding Eu(III) and Tb(III) Complexes

  • Zhang, Wei;Liu, Chang-Hui;Tang, Rui-Ren;Tang, Chang-Quan
    • Bulletin of the Korean Chemical Society
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    • v.30 no.10
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    • pp.2213-2216
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    • 2009
  • A novel carbazole functionalized bis-$\beta$-diketone type organic ligand, 1,1′-(2,6-bispyridyl)bis-3-(9-ethylcarbazole- 3-yl)-1,3-propanedione ($H_2L$) and its corresponding lanthanide complexes $Eu_2(L)_3\;and\;Tb_2(L)_3$ were successfully prepared. The ligand and complexes were characterized in detail based on FT-IR spectra, $^1H$ NMR and elemental analysis. The observed UV-Vis absorption and photoluminescence properties of the complexes were investigated, it shows that the Eu(III) and Tb(III) ions can be sensitized efficiently by the ligand ($H_2L$) to some extent, in particular, the complex $Tb_2(L)_3$ exhibits a more excellent luminescence property than the Eu(III) complex. Meanwhile, the introduction of the carbazole moiety can enlarge the $\Pi$-conjugated system of the ligand and enhance the luminescent intensity of the complexes. The results show that the complexes would be used as excellent luminescent materials.

Photoaddition Reactions of 1,2-Diketone

  • Park, Hea Jung;Seo, Jung Soo;Yoon, Ung Chan;Cho, Dae Won
    • Rapid Communication in Photoscience
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    • v.1 no.1
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    • pp.17-18
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    • 2012
  • Photoaddition reactions between 1,2-dicarbonyl compounds and silyl enol ethers in acetonitrile and benzene were explored. Irradiation of acetonitrile or benzene solutions containing 1,2-diketone, acenaphthalquinone, phenanthrene-quinone and silyl enol ethers is observed to promote the production of 1,4-dioxenes, oxetanes, and ${\beta}$-hydroxyketone by the [4+2]-cycloadditon, Paterno-Buchi processes, and SET promoted Claisen-type condensation. Among these competitive pathways leading to the generation of each types of products, SET promoted 1,4-dioxene and ${\beta}$-hydroxyketone formation are more favored regardless of solvent polarity.

Synthetic Studies on Jasmonoids(I): Jasmone, Dihydrojasmone, and Tetrahydrojasmone

  • Lee, Woo-Young;Lee, Yang-Suk;Jang, Se-Young;Lee, Sang-Yong
    • Bulletin of the Korean Chemical Society
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    • v.12 no.1
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    • pp.26-31
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    • 1991
  • Facile and efficient syntheses of terpenic perfumeries cis-jasmone, dihydrojasmone, and tetrahydrojasmone have been investigated. Cis-jasmone was synthesized by successive metallation followed by alkylation of acetone N,N-dimethylhydrazone with (Z)-2-penten-1-yl tosylate (or 2-pentyn-1-yl tosylate) and propylene oxide in one flask to give a ketonic alcohol, which was oxidized to the corresponding diketone, followed by base-catalyzed intramolecular aldol condensation to give a regioselective cyclization product. Dihydrojasmone and tetrahydrojasmone could be conveniently obtained from 2-octanone. The dimethylhydrazone of the ketone was lithiated with butyllithium and reacted with propylene oxide to give a ketonic alcohol, which was oxidized to a diketone, followed by base-catalyzed intramolecular cyclization to afford dihydrojasmone. Tetrahydrojasmone was prepared by converting the ketonic alcohol into corresponding iodoketone, followed by base-catalyzed intramolecular cycloalkylation to furnish an odoriferous product.

Synthesis, Docking Study and In-vitro Evaluation of Anti-Tuberculosis Activity of Tri Substituted Imidazoles Containing Quinoline Moiety

  • Sahana, S.;Vijayakumar, G.R.;Sivakumar, R.;Sriram, D.;Saiprasad, D.V.
    • Journal of the Korean Chemical Society
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    • v.66 no.3
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    • pp.194-201
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    • 2022
  • A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.

Photochemical Reduction of 1,2-Diketones in the Presence of $TiO_2$

  • Park, Jun U;Hong, Mi Jeong;Go, Park Gwang Hui
    • Bulletin of the Korean Chemical Society
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    • v.22 no.11
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    • pp.1213-1216
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    • 2001
  • 1,2-Diketones, camphorquinone and 1-phenyl-1,2-propanedione, are converted to the corresponding $\alpha-hydroxyketones$ in moderate to good yields by TiO2-catalyzed photochemical reactions in deoxygenated alcoholic media. The reduction yield for 1-phenyl-1,2-propanedione is considerably increased by addition of water or triethylamine