Synthesis of ferrocene-labeled steroids via copper-catalyzed azide–alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

Fehér, Klaudia; Balogh, János; Csók, Zsolt; Kégl, Tamás; Kollár, László; Skoda‐Földes, Rita

doi:10.1016/j.steroids.2012.04.005

Cited by 18 publications

(21 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At the same time, bulky substituents on either the alkyne or the azide components were found to retard the reaction, so triazoles 7ad , 7ba , 7bd and 7ca could be produced in moderate yields. It should be mentioned however, that from the series of compounds derived from azide 5c , only triazole 7ca was isolated in lower yield compared to the results obtained under homogeneous conditions …”

Section: Resultsmentioning

confidence: 78%

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Fehér

Nagy

Szabó

et al. 2018

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties.The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.

show abstract

Section: Resultsmentioning

confidence: 78%

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Fehér

Nagy

Szabó

et al. 2018

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

show abstract

“…36,46,53 The influence of steric hindrance on copper-catalyzed azide-alkyne click reaction has been reported in the preparation of ferrocene-labeled steroids with a series of azido functionalized androstanes. 39 Considerably low reactivity of 6β-azido-androstane towards ethynylferrocene was confirmed due to the steric hindrance brought by the bulky ferrocene moiety. However, when the alkynyl group and the ferrocene moiety were separated by a spacer, acceptable yield was achieved.…”

Section: The Inhibition Of Self-cyclization Of Macromonomersmentioning

confidence: 99%

Formation of long sub-chain hyperbranched poly(methyl methacrylate) based on inhibited self-cyclization of seesaw macromonomers

Chen

et al. 2016

Polym. Chem.

View full text Add to dashboard Cite

Well-defined" long-subchain hyperbranched poly(methyl methacrylate) (lsc-hp PMMA) was obtained under the reaction condition in disfavor of self-cyclization of seesaw macromonomer as well as triggered by the intrinsic hindrance of 1,1disubstituted chain ends of seesaw macromonomer. Firstly, seesaw-type alkynyl-(PMMA-Br)2 with one alkynyl group at the chain center and two bromine groups at each chain end was synthesized by atom transfer radical polymerization (ATRP). After the azidation of alkynyl-(PMMA-Br)2, seesaw macromonomer of alkynyl-(PMMA-N3)2 underwent click reaction under high concentration in a good solvent to produce lsc-hp PMMA, almost without intrachain cyclization of macromonomer. Compared with our previous reports, steric hindrance of 1,1-disubstituted MMA units endowed almost no self-cyclization of alkynyl-(PMMA-N3)2 macromonomer. Therefore, lsc-hp PMMA with exact subchain length were obtained except the polydispersity of overall molecular weight. The chemical structure of lsc-hp PMMA was fully confirmed through the combination of gel permeation chromatography (GPC) with different detectors, proton nuclear magnetic resonance spectroscopy and Fourier transform infrared analyses. Furthermore, the formation kinetics for lsc-hp PMMA was monitored based on GPC with multi-angle laser light scattering detector and followed the equation: ln[(DPw + 1)/2] = [A]0kAB,0(1 -e -αt )/α, where DPw is absolute weight-average amount of macromonomers in hyperbranched polymers."Well-defined" hyperbranched PMMA almost without self-cyclization was obtained through click reaction, facilitated by high concentration, good solvent and di-substituted chain-ends.

show abstract

“…Ascorbate-catalyzed CuAAC between AHPE and N-NBD-prop-2-ynamine was done using a modification of the reported method [8] (Figure 1). …”

Section: Azide-alkyne Cycloadditionmentioning

confidence: 99%

Synthesis and in silico evaluation of 16?-azido pregnenolone analogue as a clickable substrate for steroid-converting enzymes

2017

SDRP-JCCMM

View full text Add to dashboard Cite

Synthesis of ferrocene-labeled steroids via copper-catalyzed azide–alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

Cited by 18 publications

References 26 publications

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Formation of long sub-chain hyperbranched poly(methyl methacrylate) based on inhibited self-cyclization of seesaw macromonomers

Synthesis and in silico evaluation of 16?-azido pregnenolone analogue as a clickable substrate for steroid-converting enzymes

Contact Info

Product

Resources

About