Synthesis and properties of 5-alkynyl-1,2,3-triazoles

Domnin, I. N.; Remizova, L. A.; Старова, Галина Л.; Röminger, Frank

doi:10.1134/s1070428009110165

Cited by 9 publications

(3 citation statements)

References 9 publications

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“…The length of the C–I bond in the triazole was 2.0617(18) Å as compared to 2.097(9) Å in p -iodobenzoic acid . All bond lengths and angles were comparable to other reported triazoles. , …”

supporting

confidence: 61%

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Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents

Darwish

Blacker

Janzen

et al. 2012

ACS Med. Chem. Lett.

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A new prosthetic group referred to as the triazole appending agent (TAAG) was developed as a means to prepare targeted radioiodine-based molecular imaging and therapy agents. Tributyltin-TAAG and the fluorous analogue were synthesized in high yield using simple click chemistry and the products labeled in greater than 95% RCY with 123 I. A TAAG derivative of an inhibitor of prostate-specific membrane antigen was prepared and radiolabeled with 123 I in 85% yield where biodistribution studies in LNCap prostate cancer tumor models showed rapid clearance of the agent from nontarget tissues and tumor accumulation of 20% injected dose g −1 at 1 h. The results presented demonstrate that the TAAG group promotes minimal nonspecific binding and that labeled conjugates can achieve high tumor uptake and exquisite target-to-nontarget ratios.

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supporting

confidence: 61%

“…22 All bond lengths and angles were comparable to other reported triazoles. 23,24 To test the reactivity and stability of the I-TAAG construct, 3a was treated with Na 123 I in the presence of peracetic acid. Using 500 μg of precursor, the desired product 4b was obtained in >95% radiochemical yield and >99% radiochemical purity.…”

mentioning

confidence: 99%

Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents

Darwish

Blacker

Janzen

et al. 2012

ACS Med. Chem. Lett.

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“…The former is available in high yields via a literature known Sonogashira coupling . The latter can be produced via nucleophilic substitution of a chloro- or bromo-alcohol-derivative with NaN 3 . , Both reagents are reacted in a copper-click reaction . Following this synthetic route, 2,2′-([2,2′-bipyridine]-6,6′-diylbis(1 H -1,2,3-triazol-4,1-diyl))bis(propan-1-ol) (PrOH-BPTD) and 2,2′-([2,2′-bipyridine]-6,6′-diylbis(1 H -1,2,3-triazol-4,1-diyl))bis(ethan-1-ol) (EtOH-BPTD) are successfully produced with yields of 53 and 31%, respectively.…”

Section: Resultsmentioning

confidence: 99%

Complexation and Extraction Studies of Trivalent Actinides and Lanthanides with Water-Soluble and CHON-Compatible Ligands for the Selective Extraction of Americium

et al. 2022

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Novel hydrophilic ligands to selectively separate Am(III) are synthesized: 3,3′-([2,2′-bipyridine]-6,6′-diylbis(1H-1,2,3-triazole-4,1-diyl))bis(propan-1-ol) (PrOH-BPTD) and 3,3′-([2,2′-bipyridine]-6,6′-diylbis(1H-1,2,3-triazole-4,1-diyl))bis-(ethan-1-ol) (EtOH-BPTD). The complexation of An(III) and Ln(III) with PrOH-and EtOH-BPTD is studied by time-resolved laser fluorescence spectroscopy. [ML 2 ] 3+ is found for both Cm(III) and Eu(III), while [ML] 3+ is only formed with Cm(III). Stability constants show a preferential coordination of Cm(III) over Eu(III) with PrOH-BPTD being the stronger ligand. The distribution of Am(III), Cm(III), and Ln(III) between an organic phase containing the extracting agent N,N,N′,N′-tetra-n-octyl-3-oxapentanediamide (TODGA) and aqueous phases containing PrOH-BPTD is studied as a function of time and temperature as well as the TODGA, BPTD, and HNO 3 concentrations. A system composed of 0.2 mol/L TODGA and 0.04 mol/L PrOH-BPTD in 0.33−0.39 mol/L HNO 3 allows for selective Am(III) back-extraction into the aqueous phase while keeping Cm(III) and Ln(III) in the organic phase, marking PrOH-BPTD as an excellent complexant for an optimized AmSel process (Am(III) selective extraction).

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Intramolecular Copper(I)‐Catalyzed Interrupted Click–Acylation Domino Reaction

Larin

Lautens

2019

Angewandte Chemie

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Acyl substituted triazoles are valuable scaffolds, but the direct synthesis of these moieties from terminal alkynes by copper catalysis remains unexplored. We report a robust, general, and efficient method using a simple CuI/2,2′‐bipyridine catalytic system. This transformation involves a copper catalyzed azide‐alkyne cycloaddition (CuAAC) followed by an intramolecular acylation onto a carbamoyl chloride. The reaction proceeds under mild conditions, tolerates several functional groups, and is readily scalable. This method represents a novel strategy towards the synthesis of complex heterocycles by a CuAAC/acylation domino process.

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Synthesis and properties of 5-alkynyl-1,2,3-triazoles

Abstract: 1,3-Dipolar addition was investigated of 2-azidoethanol to diyne glycols containing primary or tertiary hydroxyethyl groups at the system of triple bonds. This reaction provided exclusively a monoadduct as a single regioisomer, namely, 5-alkynyl-1,2,3-triazole.

Cited by 9 publications

References 9 publications

Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents

Triazole Appending Agent (TAAG): A New Synthon for Preparing Iodine-Based Molecular Imaging and Radiotherapy Agents

Complexation and Extraction Studies of Trivalent Actinides and Lanthanides with Water-Soluble and CHON-Compatible Ligands for the Selective Extraction of Americium

Intramolecular Copper(I)‐Catalyzed Interrupted Click–Acylation Domino Reaction

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