• Title/Summary/Keyword: 1,3-Dipolar cycloaddition

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Synthesis of Novel 1,2-Diazepino[3,4-b]quinoxaline and Pyridazino[3,4-b]quinoxaline Derivatives (새로운 1,2-Diazepino[3,4-b]quinoxaline과 Pyridazino[3,4-b]quinoxaline)

  • Kim, Ho Sik;Jeong, Geuk
    • Journal of the Korean Chemical Society
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    • v.43 no.3
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    • pp.302-306
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    • 1999
  • The 1,3-dipolar cycloaddition reaction of the quinoxaline 4-oxide 10 with 2-chloroacrylonitrile gave the 2,3-dihydro-lH-1,2-diazepino[3,4-blquinoxalines lla, b, respectively, which were converted into the 2,3,4,6-tetrahydro-lH-l,2-diazepino[3,4-b]quinoxaline 12. The reaction of compound lla with selenium dioxide in acetic acid/water resulted in ring transformation to give the 1,4-dihydro-4-oxopyridazino[3,4-blquinoxaline 13.

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Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles

  • Sirion, Uthaiwan;Lee, Jae-Hak;Bae, Yu-Jin;Kim, Hee-Jun;Lee, Byoung-Se;Chi, Dae-Yoon
    • Bulletin of the Korean Chemical Society
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    • v.31 no.7
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    • pp.1843-1847
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    • 2010
  • An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short $Na_2SO_4$/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.

Synthesis and herbicidal activity of 3-aryltetrahydro-1,2-benzisoxazolin-4-one derivatives (3-Aryltetrahydro-1,2-benzisoxazolin-4-one 유도체의 합성 및 제초 활성)

  • Kim, Hyoung-Rae;Song, Jong-Hwan;Jeon, Dong-Ju;Hong, Kyung-Sik;Ryu, Eung-K.
    • The Korean Journal of Pesticide Science
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    • v.2 no.1
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    • pp.104-106
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    • 1998
  • 3-Aryltetrahydro-1,2-benzisoxazolin-4-one derivatives were prepared by regioselective 1,3-dipolar cycloaddition reactions of various aryl nitrile oxides with 2-cyclohexen-1-one. The structures of these compounds were designed as a modifications of triketone herbicides and showed good herbicidal activity.

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Synthesis of Pyrazolylquinoxalines and Pyrazolylpyrrolo[1,2-a]-quinoxalines (Pyrazolylquinoxaline류 및 Pyrazolylpyrrolo[1,2-a]-quinoxaline류의 합성)

  • Kim, Ho Sik;Lee, Seong Uk;Jeong, Won Young;Han, Sung Wook;Kim, Dong Il;Yoshihisa Kurasawa
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.318-324
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    • 2001
  • The reaction of 6-chloro-2-hydrazinoquinoxaline(4) or 6-chloro-2-hydrazinoquinoxaline 4-oxide(7) with alkyl (ethoxymethylene)cyanoacetates gave pyrazolylquinoxalines(5, 8). The reaction of compounds 8 with dimethyl acetylenedicarboxylate resulted in the 1,3-dipolar cycloaddition reaction and then ring transformation to afford pyrazolylpyrrolo[1,2-a]quinoxalines(9).

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Synthesis of Poly(benzyl ether) Dendrimers Containing Core Diversitiesby Click Chemistry

  • Lee, Jae-Wook;Kim, Byoung-Ki;Han, Seung-Choul;Kim, Ji-Hyeon
    • Bulletin of the Korean Chemical Society
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    • v.30 no.1
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    • pp.157-162
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    • 2009
  • General, fast, and efficient methods for the synthesis of Fréchet-type dendrimers having core diversities were elaborated. Two core building blocks, 4,4'-(3,5-bis(propargyloxy)benzyloxy)bisphenyl and N,N,N',N'-tetra(prop-2- ynyloxycarbonylethyl)-1,2-diaminoethane, were designed to serve as the alkyne functionalities for dendrimer growth via click reactions with the azide-dendrons. The synthetic strategy involved an 1,3-dipolar cycloaddition reaction between an alkyne and an azide- functionalized Fréchet-type dendrons in the presence of Cu(I) species which is known as the best example of click chemistry.

Development of Click Chemistry in Polymerization and Applications of Click Polymer

  • Karim, Md. Anwarul
    • Rubber Technology
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    • v.13 no.1
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    • pp.1-9
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    • 2012
  • Click chemistry had enjoyed a wealthy decade after it was introduced by K.B.Sharpless and his co-worker on 2001. Since there is no optimized method for synthesis of click polymer, therefore, this paper introduced three click reaction methods such as catalyst, non-catalyst and azide-end capping for fluorene-based functional click polymers. The obtained polymers have reasonable molecular weight with narrow PDI. The polymers are thermally stable and almost emitted blue light emission. The synthesized fluorene-based functional click polymers were characterized to compare the effect of click reaction methods on polymer electro-optical properties as well as device performance on quasi-solid-state dye sensitized solar cells (DSSCs) applications. The DSSCs with configuration of $SnO_2:F/TiO_2/N719$ dye/quasi-solid-state electrolyte/Pt devices were fabricated using these click polymers as a solid-state electrolyte components. Among the devices, the catalyzed click polymer composed device exhibited a high power conversion efficiency of 4.62% under AM 1.5G illumination ($100mW/cm^2$).These click polymers are promising materials in device application and $Cu^I$-catalyst 1, 3-dipolar cycloaddition click reaction is an efficient synthetic methodology.

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Synthesis of Novel D-Glucose-derived Benzyl and Alkyl 1,2,3-Triazoles as Potential Antifungal and Antibacterial Agents

  • Wei, Jin-Jian;Jin, Lei;Wan, Kun;Zhou, Cheng-He
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.229-238
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    • 2011
  • A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^{13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.

A Selective Synthesis of Isoxazolo[2,3-${\alpha}$]quinoxalines and Pyrrolo[1,2-${\alpha}$]quinoxalines by 1,3-Dipolar Cycloaddition Reaction (1,3-쌍극성 고리화 첨가반응에 의한 Isoxazolo[2,3-${\alpha}$]quinoxaline류와 Pyrrolo[1,2-${\alpha}$]quinoxaline류의 선택적인 합성)

  • Kim Ho Sik;Nam Soon Hwa;Kurasawa Yoshihisa
    • Journal of the Korean Chemical Society
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    • v.34 no.5
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    • pp.469-475
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    • 1990
  • The reaction of 2,6-dichloroquinoxaline (13) with m-chloroperbenzoic acid gave 2,6-dichloroquinoxaline 4-oxide (14), whose reaction with pyrrolidine or indoline provided 2-substituted 6-chloroquinoxaline 4-oxides (15). The isoxazolo[2,3-a]quinoxalines (16) and pyrrolo[1,2-a]quinoxalines (17) were selectively synthesized from the 2-substituted 6-chloroquinoxaline 4-oxides (15) and dimethyl acetylenedicarboxylate. Moreover, the pyrrolo[1,2-a]quinoxalines (17) were found to be produced by the ring transformation of the isoxazolo[2,3-a]quinoxalines (16).

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