• 제목/요약/키워드: C4-cycloaddition

검색결과 54건 처리시간 0.022초

CONFORMATIONAL ANALYSIS ON THE C$_4$-PHOTOCYCLODIMERS OF 4,$5^1$,8-TRIMETHYLPSORALEN

  • Kim, Ja-Hong
    • Journal of Photoscience
    • /
    • 제2권2호
    • /
    • pp.99-101
    • /
    • 1995
  • A semiempirical methods(PM3-CI-UHF, MM2) for the evaluation of ground and excited state electronic structures of electron-donating substituents are applied to 4, 5', 8-trimethylpsoralen(TMP) with TMP dimer. Three types of product have been proposed; (1) pyrone< >pyrone, (2) pyrone< >furan, (3) hetero dimer resulting from the C$_4$-cycloaddition between the furan end of one TMP moiety and the pyrone end of the other, with cis-syn configuration.

  • PDF

Photocycloaddition of 5,7-Dimethoxycoumarin to 5-Fluorouracil

  • Shim, Sang-Chul;Ra, Choon-Sup;Chae, Kyu-Ho
    • Bulletin of the Korean Chemical Society
    • /
    • 제1권4호
    • /
    • pp.121-123
    • /
    • 1980
  • $C_4$-Photocycloaddition of 5,7-dimethoxycoumarin(DMC) to 5-fluorouracil(5-FU) was studied in frozen aqueous solution. The major photoproduct was diagnosed and isolated by TLC and column chromatography. The structure of isolated photoproduct was identified as a $C_4$-cycloaddition product of DMC and 5-FU by the characteristics of its UV, IR, NMR, mass spectra, elemental analysis, and photosplitting.

Synthesis of 3-[1-(t-Butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone Derivatives

  • 서민효;이윤영;구양모
    • Bulletin of the Korean Chemical Society
    • /
    • 제17권4호
    • /
    • pp.314-321
    • /
    • 1996
  • Isoxazolidine derivatives 7 and 8 were synthesized from N-benzyl-C-(2-benzyloxyethyl)nitrones by 1,3-dipolar cycloaddition with ethyl crotonate. The isoxazolidine derivatives were converted to β-amino acid esters 9a and 9b by reduction with zinc in acetic acid. The β-amino acid esters were reacted with methylmagnesium bromide to give the 2-azetidinones (13a, 13b). The benzyl group of 2-azetidinones were removed by Birch reduction. The products were oxidized with PDC to give 3-[1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone derivatives (2a, 2c).

Photoreaction of 8-Methoxypsoralen with Thymine

  • Shim, Sang-Chul;Kim, Yong-Zu
    • Bulletin of the Korean Chemical Society
    • /
    • 제4권2호
    • /
    • pp.95-99
    • /
    • 1983
  • Photoreaction of 8-methoxypsoralen (8-MOP) with thymine (${\ge}$ 300 nm) was carried out in the dioxane-water frozen state. One major and two minor monoaddition products between 8-MOP and thymine were isolated by various chromatographic methods. Major monoadduct was characterized to be a C4 cycloaddition product formed between 5,6-double bond of thymine and 3,4-double bond of 8-MOP with cis-anti stereochemistry. Two minor adducts were proved to be stereoisomers of this major adduct.

Theoretical Studies on the Photochemical Reaction of Psoralen with Purine and Pyrimidine Base

  • Kim Ja Hong;Sohn Sung Ho
    • Bulletin of the Korean Chemical Society
    • /
    • 제13권2호
    • /
    • pp.173-176
    • /
    • 1992
  • The spectroscopic studies of the 5,7-dimethoxycoumarin(5,7-DMC) and 4,5',8-trimethylpsoralen(TMP) and the conformational stability of 5,7-DMC-thymidine, 4,5',8-TMP-thymine were carried out by the CNDO/S and molecular mechanics calculation. Theoretical transition energies and direction of polarizations calculated by the CNDO/S method have been used for the interpretation of the observed results. The calculated absorption spectra of 5,7-DMC are qualitatively similar to experimental ones with their characteristic visible bands. MM2 force field calculation on the possible $C_4-cyclophotoadducts$ formed between 5,7-DMC and thymidine through a cycloaddition. of $C_3$, $C_4$ bond of 5,6-DMC to $C_5$, $C_6$ bond of thymidine showed the most stable photocycloadduct to have the anti-head to tail configuration. The major photoadduct of 4,5',8-TMP-thymine has the cis-anti configuration.

Sonochemical Synthesis of Closed [5,6]-bridged Aziridino[70]fullerene Derivative and Self-assembled Multilayer Films

  • Yoon, Shin-Sook;Hwang, Sung-Ho;Hong, Sung-Kyu;Lee, Jeong-Ho;Ko, Weon-Bae
    • Carbon letters
    • /
    • 제10권4호
    • /
    • pp.325-328
    • /
    • 2009
  • This cycloaddition of [70]fullerene with methyl azidoacetate in benzene under ultrasonic irradiated condition afforded the closed [5,6]-bridged aziridino[70]fullerene derivative, which was unusual product of cycloaddition to the 5,6-junction of fullerene. Its structure was determined by FAB-MS, UV-vis, $^1H-$ and $^{13}C$-NMR spectral data. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films were self-assembled using the layer-by-layer method on the reactive of glass slides functionalized with 3-mercaptopropyl trimethoxysilane. The functionalized glass slides were alternately soaked in the solution containing closed the [5,6]-bridged aziridino[70]fullerene and 4-aminothiophenoxide/hexanethiolate-protected gold nanoparticles. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films have grown up to 5 layers depending on the immersion time. The self-assembled nanoparticle multilayer films were characterized using UV-vis spectroscopy showed that the surface plasmon band of gold at 527 nm gradually became more evident as successive layers were added to the films.

항진균성항생물질 griseofulvin 유도체인 6'-phenylgriseofulvin의 합성과 항균활성 (Synthesis and biological activity of 6'-phenylgriseofulvin as analogs of antibiotic griseofulvin)

  • 고병섭;절곡륭지;산하공평
    • Applied Biological Chemistry
    • /
    • 제35권5호
    • /
    • pp.395-398
    • /
    • 1992
  • Griseofulvin의 구조활성상관연구에서 6'-methyl기와 4'-oxo기가 생물활성에 있어서 중요한 인자라는 것이 예견되어, 6'-methyl기(基)를 phenyl기(基)로 치환한 6'-phenylgriseofulvin을 diels-alder부가환화로 합성하고 Botrytis allii 및 B. cinerea에 대한 항균활성을 paper disc 법으로 연구하였다. 6'-Phenylgriseofulvin은 $25\;{\mu}g/disc$에서 높은 항균활성을 나타냈다.

  • PDF

1,2,4-Triazole Fused Heterocycles; Part 3. Preparation of 1-(1-Phenylethenyl)-5-(N-substituted amino)-1,2,4-triazoles and 4H-1,2,4-Triazolo[1,5-c][1,3,5]oxadiazines

  • 이기정;이유석;송동혁
    • Bulletin of the Korean Chemical Society
    • /
    • 제16권11호
    • /
    • pp.1037-1042
    • /
    • 1995
  • The reaction of acetophenone 1-ureidoethylidenehydrazones 6 with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine in dichloromethane provides a general route to 1-(1-phenylethenyl)-5-(N-substituted amino)-1,2,4-triazoles 11 via the electrocyclization of the expected azino carbodiimide intermediates 9 to give the resonance stabilized azomethine imine 10a followed by a proton abstraction from the methyl group by amide anion. However, the same reaction of benzaldehyde 1-ureidoethylidenehydrazones 5 was unsuccessful. Under the same conditions, the reactions of benzaldehyde 1-N-acylureidoethylidenehydrazones 7 or acetophenone 1-N-acylureidoethylidenehydrazones 8 afforded 4H-1,2,4-triazolo[1,5-c][1,3,5]oxadiazines 16 or 17 via the zwitterionic species 15, or a [4+2] intramolecular cycloaddition from the carbodiimide intermediates 14, respectively.

부틸글리시딜에테르와 이산화탄소의 부가반응에 대한 이온성 액체의 촉매 성능 고찰 (Catalytic Performance of Ionic Liquids for the Cycloaddition of Carbon Dioxide and Butyl Glycidyl Ether)

  • 박대원;주혜영;이미경
    • 한국응용과학기술학회지
    • /
    • 제25권4호
    • /
    • pp.469-476
    • /
    • 2008
  • The synthesis of cyclic carbonate from butyl glycidyl ether (BGE) and carbon dioxide was performed in the presence of three different types of ionic liquid : quarternary ammonium salt, alkyl pyridinium salt, and alkylimidazolium salt. Ionic liquids of different alkyl groups ($C_3$, $C_4$, $C_6$ and $C_8$) and anions ($Cl^-$, $Br^-$ and $I^-$) were used for the reaction which was carried out in a batch autoclave reactor at $60{\sim}120^{\circ}C$. The catalytic activity was increased with increasing alkyl chain length in the order of $C_3$ < $C_4$ < $C_6$. But the ionic liquid with longer alkyl chain length ($C_8$) decreased the conversion of BGE because it is too bulky to form an intermediate with BGE. For the counter anion of the ionic liquid catalysts, the BGE conversion decreased in the order $Cl^-$ > $Br^-$ > $I^-$.