• Title/Summary/Keyword: intramolecular cyclization

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Synthesis of 2-(Pyrazol-1-yl)quinoxalines and 2,3-Di(pyrazol-1-yl)quinoxalines (2-(Pyrazol-1-yl)quinoxaline류 및 2,3-Di(pyrazol-1-yl)quinoxaline류의 합성)

  • Kim, Ho-Sik;Jeong, Won-Young;Choi, Kyung-Ok;Lee, Seong-Uk;Kwag, Sam-Tag;Lee, Man-Kil
    • Journal of the Korean Chemical Society
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    • v.46 no.1
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    • pp.37-45
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    • 2002
  • The reaction of 3,6-dichloro-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(8) or 6-chloro-3-hydrazino-2-(3,5-dimethylpyrazol-1-yl)quinoxaline(9) with substituted anilines, sulfa drugs and heteroacyl chlorides gave 2-(pyrazol-1-yl)quinoxalines(10-12). The reaction of compound 9 with alkyl (ethoxymeth-ylene) cyanoacetates resulted in the intramolecular cyclization to give 2,3-di(pyrazol-1-yl)quinoxalines(13).

Synthesis and Tautomerism of Novel Quinoxalines (Part I) (새로운 Quinoxaline류의 합성과 토토머화 현상 (제1보))

  • Ho Sik Kim;Jin Hee Kim
    • Journal of the Korean Chemical Society
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    • v.47 no.3
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    • pp.241-249
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    • 2003
  • The reaction of 3-(1-ethoxycarbonyl)ethyl-1,2-dihydro-2-oxoquinoxaline (8) with hydrazine hydrate gave 3-(1-hydrazinocarbonyl)ethyl-2-hydroxyquinoxaline (9). The reaction of compound 9 with substituted benzaldehydes and heteroaryl aldehydes afforded 2-hydroxyquinoxalines (10-12), respectively. The reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates and ethoxymethylenemalononitrile resulted in the intramolecular cyclization to give the 5-amino-1-[2-(3-hydroxyquinoxalin-2-yl)propanoyl]-pyrazoles (13), respectively. Compounds 10-13 showed the tautomerism between the lactam and lactim forms in dimethyl sulfoxide solution. The tautomer ratios were determined by the $^1H$ NMR. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

Facile Formation of Unexpected [m,6,n]-tricyclic Spiranes via Intramolecular [3+2] Cyclization of Platinum-bound Pyrylium with Alkenes

  • Oh, Chang-Ho;Tak, Sang-Yong;Lee, Ji-Ho;Piao, Lanhua
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.2978-2980
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    • 2011
  • Enynals bearing an olefinic pendant were successfully cyclized via Huisgen-type [3+2] cycloaddition to the tetracyclic Pt-carbene complexes which would undergo insertion into a C-H bond of the ${\beta}$-position to afford the fused cyclopropane intermediates. Their tandem rearrangement afforded diverse types of spiranes depending on the tethered alkenes of the enynals.

Cylization Reaction of 2 (2', 2'-diethoxy ethyl) Aminobenzamide derivatives (II) (2(2',2'-디에톡시 에틸)아미노벤즈아미드 유도체의 고리화반응(II))

  • Yoo, Hee-Weon;Lee, Jin-Wha;Suh, Myung-Eun
    • YAKHAK HOEJI
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    • v.33 no.4
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    • pp.246-252
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    • 1989
  • 2-Amino-1-N-methyl benzamide, 2-N-benzyl amino benzamide, 2-N-phenyl amino benzamide of 2-amino benzamide derivatives were reacted with ${\alpha}-bromo$ acetaldehyde diethyl acetal in basic condition. 2-N-alkylated products were prepared from 2-amino-1-N-methyl benzamide and 2-N-phenyl amino benzamide. 1-N-benzyl-1.4-benzodiazepin-5-one was prerpared from 2-N-benzyl aminobenzamide via intramolecular cyclization. However, 2-amino-1-N-methyl benzamide with sodium amide did not react to 1.4-benzodiazepin-5-one derivative but 3-methyl-quinazoline-2.4-dione was obtained.

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Photochemistry of 1-(o-substituted -phenyl)-2-pentamethyldishilanyl Ethynes

  • Shim, Sang-Chul;Park, Seung-Ki
    • Journal of Photoscience
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    • v.6 no.1
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    • pp.13-19
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    • 1999
  • Irradiation of 1-(o-allyloxyphenyl)-2-pentamethyldisilanylenthyne 2a in methanol yields two 1 : 1 photoaddition products 3 and 4 via silacyclopropene intermediate. Photolysis of 2a with acetone in deaerated methylene chloride yields site specific and regioselective 1 : 1 adducts 6 ad 7 via silacyclopropene and 1-sila-1, 2-propdiene intermediate, respectively. Photolysis of 2a and 1-(o-(3', 3'-dimethyl-2'-propenylox)phenyl)-2-pen-tamethyldisilanylethyone 2b in benzene provides novel stereoselevtive intramolecular cyclization products 10 and 11, respectively. Irradiation of 1-(o-acetoxyphenyl)-2-pentamethyldisilanyl ethyne 2c in benzene yields the photo-Fries rearrangement products 18 and 19 and a photoproduct 17 via silacyclopropene intermediate. Photolysis of 1-(o-methoxycarbonlymethoxyphenyl)-2-pentamethyl disilanylenthyne 2d in benzene provides a novel intramolecular cycloaddition product 25 and 1-(o-methoxycarbonylemthoxiyphenyl)-2-trimethylsilylethyne 26 via silacyclopropene intermediate.

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A Novel Photoreaction of (2-Hydroxyethoxyphenyl)pentamethyldisilane

  • Park, Seung Ki;Seong, Won-Je
    • Bulletin of the Korean Chemical Society
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    • v.30 no.6
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    • pp.1331-1336
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    • 2009
  • Photolysis of (2-hydroxyethoxyphenyl)pentamethyldisilane 2 in benzene provides a novel intramolecular cyclization photoproduct 9 which was probably formed from the intramolecular reaction to form a seven-membered ring in silatriene intermediate 7 and then the photochemical disrotatory ring closure of 1,3-butadiene moiety to cyclobutene. Irradiation of 2 in methanol afforded photoproducts 5 and 6 which were formed by the nucleophilic attack of methanol to $\beta$ or $\alpha$ silicon atom in pentamethyldisilanyl group of the photoexcited state of 2. Compounds 10 and 11 were also formed by the same way as in the formation of the photoproducts 5 and 6 in the photolysis of (2-allyloxyethoxyphenyl)pentamethyldisilane 3 in methanol solvent. Photoreaction of (2-acetoxyethoxyphenyl) pentamethyldisilane 4 in methanol gave a photoproduct 12 which was formed via the elimination of dimethylsilylene species in the photoexcited state of 4.

Recent Liquid Crystal Material Development for VA-TFT

  • Bremer, Matthias
    • 한국정보디스플레이학회:학술대회논문집
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    • 2005.07b
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    • pp.1067-1070
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    • 2005
  • A large size flat panel LCD-TV must fulfill different requirements than a desktop LCD-monitor: The contrast must be much larger, the viewing angle should be as wide as possible and the switching times must be shorter to allow moving pictures to be displayed naturally. The "Vertically Aligned" technology is most promising to realize such a product. LC-material development for this technology began at Merck about 10 years ago. New materials based on the 1,1,6,7-tetrafluoroindane skeleton were recently synthesized via ortho-metallation and intramolecular Heck cyclization followed by an oxidative fluorination procedure. The materials offer improved properties over liquid crystals currently employed in flat panel LCD-TVs.

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A Facile One-Pot Operations of Reduction and Allylation of Nitrobenzaldehydes Mediated by Indium and Their Applications

  • Cho, Yong-Seo;Kang, Kyung-Ho;Cha, Joo-Hwan;Choi, Kyung-Il;Pae, Ae-Nim;Koh, Hun-Yeong;Chang, Moon-Ho
    • Bulletin of the Korean Chemical Society
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    • v.23 no.9
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    • pp.1285-1290
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    • 2002
  • Various nitrobenzaldehydes were simultaneously allylated and reduced using indium in the presence of HCl in aqueous media to give compounds having both functionality of homoallylic alcohol and aromatic amine. Sequential protection of the amino gro up and oxidation of the anilinyl homoallylic alcohol provided useful precursors of heterocyclic compounds such as dihydroindolones and dihydroquinolones, which could be efficiently synthesized through intramolecular cyclization reaction.