• Title/Summary/Keyword: Thiophenes

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Facile Regiocontrolled Three-Step Synthesis of Poly-Substituted Furans, Pyrroles, and Thiophenes: Consecutive Michael Addition of Methyl Cyanoacetate to α,β-Enone, CuI-Mediated Aerobic Oxidation, and Acid-Catalyzed Paal-Knorr Synthesis

  • Kim, Se-Hee;Lim, Jin-Woo;Lim, Cheol-Hee;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.2
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    • pp.620-624
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    • 2012
  • An efficient synthesis of poly-substituted furans, pyrroles, and thiophenes was carried out in a regiocontrolled manner via a three-step process; (i) conjugate addition of methyl cyanoacetate derivatives to ${\alpha}$,${\beta}$-enones, (ii) CuI-mediated aerobic oxidation, and (iii) Paal-Knorr type synthesis of five-membered heterocycles.

경유의 Model solution에서 고정화효소를 이용한 Dibezothiophene의 산화

  • Heo, Jeong-Chan;Seong, Hyeon-Tae;Ryu, Geun-Gap
    • 한국생물공학회:학술대회논문집
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    • 2001.11a
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    • pp.517-520
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    • 2001
  • Fossil fuels such as coal and crude oil contain various organic sulfur compounds. Combustion of these fuels emit sulfur oxides which are considered as msjor air pollutants causing acid rain problem. Among various organic sulfur compounds, aromatic sulfur compounds of thiophenes which constitute major sulfur fractions of heavy oils are not easily removed by hydrodesulfurization. Many peroxidase and hemoproteins are known to oxidize dibenzothiophene (DBT) to dibenzothiophene-sulfoxide(DBT - sulfoxide) then dibenzothiophene- sulfone (DBT-sulfone). The oxidation of DBT by the immobilized hemoproteins in n-octane was increased significantly when the hemoproteins were deposited on celites of the particle size between 0.75 - 1.0 mm and a conventional substrates. such as t-butyl hydroperoxide and cumene hydroperoxide. In anhydrous organic solvents with log P values larger than 4.0 DBT was completely oxidized by cumene hydroperoxide catalyzed by cytochrome c deposited on celites.

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MO Studies of Configuration and Conformation (Ⅲ). Conformations of Some 2-Substituted Furan, Thiophene and Pyrrole Carbonyl Compounds (配置와 形態에 관한 分子軌道函數論的 硏究 (第3報). Furan, Thiophene 및 Pyrrole 카르보닐 化合物의 2-置換體의 形態)

  • Ikchoon Lee;Shi Choon Kim
    • Journal of the Korean Chemical Society
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    • v.21 no.1
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    • pp.32-37
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    • 1977
  • Conformations of nine 2-substituted furan, thiophene and pyrrole compounds have been studied by EHT methods. The preferred conformations of furan derivatives were trans form, which were mainly stabilized by electrostatic interactions. For thiophenes, electronic conjugation between the ring S and carbonyl oxygen was dominant, while for pyrroles both the electrostatic and conjugation effects were operative in determining the preferred conformations. Results of EHT calculation agreed well with experimentally determined preferences.

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Synthesis of New Heterocycles Derived from 3-(3-Methyl-1H-indol-2-yl)-3-oxopropanenitrile as Potent Antifungal Agents

  • Gomha, Sobhi M.;Abdel-Aziz, Hatem A.
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.2985-2990
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    • 2012
  • New thiazoline derivatives 7a-c, and thiophenes 9a-c linked to indole moiety were easily prepared via the reaction of the acrylamide derivative 3 with phenacyl bromides 4a-c, depending on the reaction conditions. In addition, the reaction of compound 3 with hydrazonoyl chlorides 11a-f afforded a series of 1,3,4-thiadiazole derivatives 13a-f. Moreover, coupling of 3-(3-methyl-1H-indol-2-yl)-3-oxopropanenitrile (2) with the diazonium salts of 3-phenyl-5-aminopyrazole 16 or 3-amino-1,2,4-triazole 17 gave the corresponding hydrazones 18 and 19, respectively. Cyclization of the latter hydrazones yielded the corresponding pyrazolo[5,1-c]-1,2,4-triazine and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives 20 and 21, respectively. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, $^1H$ NMR and mass spectral data. All the synthesized compounds were tested for in vitro activities against certain strains of fungi such as Aspergillus niger, Aspergillus nodulans, Alternaria alternate. Compounds showed marked inhibition of fungal growth nearly equal to the standards.

Microwave Assisted Reaction of Condensed Thiophenes With Electron Poor Olefins

  • Al-zaydi, Khadijah M.;Elnagdi , Mohamed H.
    • Journal of the Korean Chemical Society
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    • v.47 no.6
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    • pp.591-596
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    • 2003
  • Aminothienopyridazines 1a, b and aminothienocoumarin 2 condensed with DMFDMA to yield amidines 3a, b and 4. These compounds reacted with N-phenylmaleimide to yield 9 and 10. On the other hand reacting 3a, b, 4, 18, 19 and 20 with maleic anhydride afforded only the formylated derivatives 5a, b, 6, 21, 22 and 23 respectively. The reaction of 3a, b with diethyl fumarate afforded 11, formed most likely via hydrolysis of the amidine 14 during working up the reaction mixture. Irradiation of N-phenylmaleimide in microwave oven afforded [2+2] and [2+2+2] cycloaddition product.

Volatile Flavor Components in Green Tea Blended with Parched Naked Barley (볶은 쌀보리를 혼합한 녹차의 휘발성 향기성분)

  • Choi, Sung-Hee
    • Journal of Life Science
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    • v.22 no.7
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    • pp.981-986
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    • 2012
  • To produce a new tea with a good flavor and functional properties using green tea of low quality, naked barley and barley were selected to blend with the green tea. The simultaneous distillation extraction method (SDE) using Likens and Nickerson's extraction apparatus was used to extract the volatile flavor compounds from the samples. The concentrated flavor extracts were analyzed and identified by GC and GC-MS. The GC patterns of the flavor components in two parched barleys were very different. The main volatile flavor components in two of the samples were alkyl pyrazines. Compounds including 3-methylbutanal, 2-methylbutanal, dihydro-2-methyl-3(2H)-furanone, 2,5-dimethyl pyrazine, and 3-ethyl-2.5-dimethyl pyrazine were isolated from the naked barley. Compounds including thiophenes, thiazoles, sulfides, and pyrroles with burnt odor were isolated from the barley. The parched naked barley was better than barley for adding to green tea. The main aroma components of the green tea blended with the naked barley were hexanol, hexanal, trans-2-hexenal, ${\beta}$-ionone, ${\alpha}$-ionone, alkyl pyrazines, 3-methylbutanal, 2-methylbutanal, and furfural.

Synthesis and Characterization of Bis-Thienyl-9,10-anthracenes Containing Electron Withdrawing 2-Cyanoacrylic Acid or 2-Methylenemalononitrile Group

  • Wang, Yuan;Yu, Qu Feng;Park, Hea-Jung;Ryu, Suk-Hwa;Choi, Jung-Hei;Yoon, Ung-Chan
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.3081-3089
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    • 2011
  • A series of new bis-thienylanthracene derivatives D1~D5 containing 9,10-antharcene moiety in the center and 2-methylenemalonotitrile or 2-cyanoacrylic acid functional group on the terminal thiophenes were synthesized and characterized by $^1H$-NMR and high-resolution mass spectroscopy. Their optical, electrochemical, and thermal properties were measured. They have absorption ${\lambda}_{max}$ in the range of 437~480 nm and max of $7.4{\times}10^3{\sim}2.0{\times}10^4M^{-1}cm^{-1}$. The substitution of 2-cyanoacrylic acid group allows greater value of ${\varepsilon}_{max}$ than that of 2-methylenemalonotitrile. TGA curves showed that D4 and D5 which have 2-cyanoacrylic acid functional group on the terminal thiophene(s) exhibit good thermal stability and D4 was thermally stable up to $400^{\circ}C$. Their optical properties and LUMO energy levels measured suggest that they can serve as potential candidates for electron donor materials of organic photovoltaic cells (OPVs) or D4 and D5 which contain 2-cyanoacrylic acid group can be used as organic dyes of dye-sensitized solar cells (DSSCs).

A First Synthesis and Physical Properties of Asymmetric Anthracenes-Thiophenes Bridged with Ethylene

  • Hwang, Min Ji;Park, Ji Hee;Jeong, Eun Bin;Kang, Il;Lee, Dong Hoon;Park, Chan Eon;Singh, O.M.;Choi, HoJune;Kim, Yoon-Hi;Yoon, Yong Jin;Kwon, Soon-Ki;Lee, Sang-Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3810-3816
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    • 2012
  • Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of $2.6{\times}10^{-2}cm^2/Vs$ and $4.4{\times}10^{-3}cm^2/Vs$, respectively, in solution processed OTFTs.