• Title/Summary/Keyword: Azide-alkyne cycloaddition

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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.

Diastereomeric Strain-Promoted Azide-Alkyne Cycloaddition: determination of configuration with the 2D NMR techniques

  • Hye Jin Jeong
    • Journal of the Korean Magnetic Resonance Society
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    • v.27 no.2
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    • pp.10-15
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    • 2023
  • The Strain-Promoted Azide-Alkyne Cycloaddition (SPAAC) is a powerful method for synthesizing triazoles, even under physiological conditions, without a copper catalyst. This technique provides an efficient means for everyone to synthesize complex triazole derivatives rapidly. In order to investigate the configuration of triazole derivatives using bicyclo[6.1.0.]-nonyne (BCN) and chiral azide, it is necessary to employ the 2D NMR. Both 1D and 2D NMR (COSY, HSQC, 15N HMBC) are used to analyze the complex triazole product containing cyclooctyne, a diastereomeric product. The stereometric difference of the proton bonded to the same carbon is determined through the HSQC assignment. The intriguing splitting pattern of carbon resonances also reveals their diastereomeric configuration and will aid in further research based on physiological knowledge.

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.

Entry to Highly Hindered Chiral β-Amino Triazoles Bearing a gem-Diaryl Group by Azide-alkyne Click Chemistry

  • Sadu, Venkata Subbaiah;Roy, Harendra Nath;Arigala, Pitchaiah;Hwang, In-Taek;Lee, Kee-In
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1605-1612
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    • 2014
  • Copper(I)-catalyzed Huisgen cycloaddition of terminal alkynes with unmasked azidoamines derived from amino acids is described. The reported strategy provides a new entry to highly hindered ${\beta}$-amino 1,2,3-triazole derivatives bearing a gem-diaryl group, which are potentially valuable entities as molecular catalysts for asymmetric transformations.

Strain-promoted alkyne-azide cycloaddition for PET molecular imaging study

  • Jeong, Hyeon Jin;Kim, Dong Wook
    • Journal of Radiopharmaceuticals and Molecular Probes
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    • v.1 no.1
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    • pp.15-22
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    • 2015
  • $^{18}F$-labeling reaction of bioactive molecule via click chemistry is widely used to produce $^{18}F$-labeled radiotracer in the field of radiopharmaceutical science and molecular imaging. In particular, bioorthogonal strain-promoted alkyne-azide cycloaddition (SPAAC) reaction has received much attention as an alternative ligation method for radiolabeling bioactive molecules such as peptides, DNA, proteins as well as nanoparticles. Moreover, SPAAC based pretargeting method could provide tumor images successfully on positron emission tomography system using nanoparticle such as mesoporous silica nanoparticles.

Synthesis of Poly(benzyl ether) Dendrimers by Click Chemistry (클릭 화학에 의한 폴리(벤질에테르)덴드리머의 효율적인 합성)

  • Lee, Jae-Wook;Lee, Un-Yup;Han, Seung-Choul;Kim, Ji-Hyeon;Jin, Sung-Ho
    • Polymer(Korea)
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    • v.33 no.1
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    • pp.67-71
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    • 2009
  • The stitching method for the synthesis of $Fr\acute{e}chet$-type dendrimers was elaborated using click chemistry between an alkyne and an azide. The core building block, 4,4'-(3,5-bis(azidopropyloxy)benzyloxy)bisphenyl, was designed to serve as the azide functionalities for dendrimer growth via click reactions with the alkyne-dendrons. The synthetic strategy involved an 1,3-dipolar cycloaddition reaction between an azide and an alkyne-functionalized $Fr\acute{e}chet$-type dendrons in the presence of Cu(I) species which is known as the best example of click chemistry.

Convergent Synthesis of PAMAM-like Dendrimers from Azide-functionalized PAMAM Dendrons

  • Lee, Jae-Wook;Kim, Jung-Hwan;Kim, Byung-Ku;Kim, Ji-Hyeon;Shin, Won-Suk;Jin, Sung-Ho;Kim, Myung-hak
    • Bulletin of the Korean Chemical Society
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    • v.27 no.11
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    • pp.1795-1800
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    • 2006
  • The convergent synthesis of symmetric PAMAM-like dendrimers from azide-functionalized poly(amido- amine) (PAMAM) dendrons and two different multi-alkynes was investigated. The stitching method was based on the click chemistry protocol, i.e., the copper-catalyzed cycloaddition reaction between an alkyne and an azide.

Synthesis of Dendrimer with PEG Core by Click Chemistry (클릭 화학에 의한 PEG 핵을 갖는 덴드리머의 합성)

  • Han, Seung-Choul;Jin, Sung-Ho;Lee, Jae-Wook
    • Polymer(Korea)
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    • v.36 no.3
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    • pp.295-301
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    • 2012
  • Efficient stitching methods for the synthesis of Fr$\acute{e}$chet-type dendrimers with linear PEG units at a core were elaborated. The synthetic strategy involved an inexpensive 1,3-dipolar cycloaddition reaction between an alkyne and an azide in the presence of Cu(I) species which is known as the best example of click chemistry. The linear core building blocks, two diazido-PEG units, were chosen to serve as the azide functionalities for dendrimer growth via click reactions with the alkyne-dendrons. These two building blocks were employed together with the alkyne-functionalized Fr$\acute{e}$chet-type dendrons in a convergent strategy to synthesize two kinds of Fr$\acute{e}$chet-type dendrimers with different linear core units.

Facile Synthesis of Dendritic-Linear-Dendritic Materials by Click Chemistry

  • Lee, Jae-Wook;Han, Seung-Choul;Kim, Byoung-Ki;Lee, Un-Yup;Sung, Sae-Reum;Kang, Hwa-Shin;Kim, Ji-Hyeon;Jin, Sung-Ho
    • Macromolecular Research
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    • v.17 no.7
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    • pp.499-505
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    • 2009
  • General, fast, and efficient stitching methods are presented for the synthesis of Fr$\acute{e}$chet-type dendrimers with linear units at a core, as a preliminary investigation for the synthesis of dendritic-linear-dendritic materials. The synthetic strategy involved an inexpensive, 1,3-dipolar, cycloaddition reaction between an alkyne and an azide in the presence of the Cu(I) species, which is known as the best example of click chemistry. The linear core building blocks, 1,7-octadiyne and 1,6-diazidohexane, were chosen to serve as the alkyne and azide functionalities for dendrimer growth via click reactions with the azide and alkyne-dendrons, respectively. These two building blocks were employed together with the azide- and alkyne-functionalized Fr$\acute{e}$chet-type dendrons in a convergent strategy to synthesize two kinds of Fr$\acute{e}$chet-type dendrimers with different linear core units. This comparative efficiency of the click methodology supports the fast and efficient synthesis of dendritic-linear-dendritic materials with the tailor made core unit.

Synthesis of Dendrimer Containing Dialkylated-fluorene Unit as a Core Chromophore via Click Chemistry

  • Han, Seung-Choul;Jin, Sung-Ho;Lee, Jae-Wook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.1
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    • pp.137-142
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    • 2012
  • The convergent synthetic strategy for the emissive dendrimers having the chromophore at core via the coppercatalyzed 1,3-dipolar cycloaddition reaction between alkyne and azide was described. 2,7-Diazido-9,9-dioctyl-9H-fluorene, designed to serve as the core in dendrimer, was stitched with the alkyne-functionalized Frechettype and PAMAM dendrons by the click chemistry leading to the formation of the corresponding fluorescent dendrimers in high yields. The preliminary photoluminescence studies indicated that 2,7-diazido-9,9-dioctyl-9H-fluorene showed no fluorescence due to the quenching effect from the electron-rich ${\alpha}$-nitrogen of the azido group but the dendrimers fluoresced due to the elimination of the quenching through the formation of the triazole ring.