• Title/Summary/Keyword: 1,3 Dipolar Reaction

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Effect of Themperature on the 1,3-dipolar Cycloaddition of 3-phenyloxadiazole Derivatives (3-Phenyloxadiazole 유도체의 1,3-dipolar Cycloaddition 반응에 미치는 온도의 영향)

  • Hwang, Sung-Kwy;Lee, Ki-Chang;Choi, Bong-Jong;Lee, Kwang-Ill
    • Journal of the Korean Applied Science and Technology
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    • v.14 no.3
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    • pp.39-46
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    • 1997
  • Ultraviolet spectrophotometric investigation has been carried out on the rate constants for 1,3-dipolar cycloaddition of 4-substituted-3-phenyloxadiazole derivatives with dipolarophiles such as phenyl acetylene, propiolic acid methyl ester and dimethylacetylene dicarboxylate. From there, the rate constants for 1,3-dipolar cycloaddition were determined at 80, 100 and $120^{\circ}C$, and the reaction rates were increased with increasing temperature. From these rate constants, the values of the thermodynamic activation parameters were obtained. Some thermodynamic activation parameters such as $E_{\alpha}$, ${\Delta}H^{\ast}$, ${\Delta}S^{\ast}$ and ${\Delta}G^{\ast}$ from Arrhenius equation were also calculated for the electrophilic 1,3-dipolar cycloaddition of 3-phenyloxadiazole derivatives with dipolarophiles. In order to the proposal the mechanism and reactivity of 1,3-dipolar cycloaddition reaction, the effect of substituents having various kinds of electron withdrawing or releasing groups were examinated. Considering the effect of substituents, an electron withdrawing group attached at the 4-carbon position in 3-phenyloxadiazole derivatives decreases the reaction rate because of the lack of electron density in 3-phenyloxadiazole ring.

Synthesis and Antibacterial Activity of New Tetrazole Derivatives (새로운 Tetrazole유도체의 합성과 항균활성)

  • Mulwad, V.V.;Pawar, Rupesh B;Chaskar, Atul C
    • Journal of the Korean Chemical Society
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    • v.52 no.3
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    • pp.249-256
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    • 2008
  • 3-Acetyl/Formyl 4-hydroxy-2H(1)-benzopyran-2-one on treatment with malonitrile and ethyl cyanoacetate yielded 1,1-dicyano-2-[4/-hydroxy-2/H(1)-benzopyran-2/-one-3/-yl] ethene/propene 2a-h and ethyl-2-cyano-3-[4/-hydroxy-2/H (1)-benzopyran-2/-one-3/-yl] propenoate/butenoate 3a-h respectively. The 1,3 dipolar reaction of 2a-h with NaN3 gave the tetrazole derivative 4a-h. 3a-h on cyclization with PPA gave 3-cyano-2H,5H-pyrano [3, 2-c] benzopyran-2,5-diones 5a-h which on 1,3 dipolar reaction with NaN3 to gave 3-(1/H-tetrazol-5/-yl)-2H,5H-pyrano[3, 2-c] benzopyran-2,5-diones 6a-h. The structures of the compounds have been established on the basis of the spectral and analytical data. All the compounds were screened for their antimicrobial activities and have been found to exhibited significant antibacterial activities. Compounds 2h and 4h showed the activity 50g/mL.

Synthesis of Novel 1,2-Diazepino[3,4-b] quinoxalines and pyridazino[3,4-b] quinoxalines (새로운 1,2-다이아제피노 [3,4-b]퀴녹살린류와 피리다지노 [3,4-b] 퀴녹살린류의 합성)

  • Kim, Ho-Sik;Lee, Seong-Uk;Jeong, Geuk;Lee, Man-Kil;Kurasawa, Yoshihisa
    • YAKHAK HOEJI
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    • v.44 no.4
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    • pp.325-333
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    • 2000
  • The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxides 2 with 2-chloroacrylonitrile gave the 2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxalines 3, which were converted into the 2,3,4,6-tetrahydro-1H-1,2-diazepino[3,4-b]quinoxalines 5-7. The reaction of compounds 3 with selenium dioxide in acetic acid/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-b]quinoxalines 8.

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Total synthesis of Antofine by using Intramolecular 1.3-dipolar cycloaddition of Azidealkene

  • Lee, Jae-Kwang;Lee, Tae-Ho;Song , So-Young
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.362.2-362.2
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    • 2002
  • Antofine belongs to the Phenathroindolizidine group of alkaloids. This natural products exhibit interesting biological properties such as antitumour activity. and anti-inflammentory. Wittig reaction of phenathrenealdehyde with the phosponium salt provided the phenathreneazidealkene in good yield. Intramolecular 1.3-dipolar cycloaddition of the resulting azidealkent in refluxing benzene proceeded the imine. It was reduced with cyanoborohydride of Noyori's Asymmetric Hydrogenation. (omitted)

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Kinetics of the 1,3-dipolar Cycloaddition of p-substituted 3-phenylsydnones with DMAD

  • Youn, Byoung-Hee;Lyu, Hak-Soo;Han, Jee-Hyun;Hahn, Soon-Jong;Kim, Sun-Hwan
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.233-235
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    • 1987
  • The kinetics of the 1,3-dipolar cycloaddition of p-substituted 3-phenylsydnones 1a-d with DMAD have been investigated. The reaction rates over a temperature range $100-140^{\circ}C$ were measured by UV spectrometry. The reactions found to be second-order overall, insensitive to the dielectric constants of the solvents, and characterized by a large entropy of activation. These findings are consistent with the rate-determining step involving the formation of cyclic transition state 1 and the reaction proposed to be concerted.