4790-35-6Relevant academic research and scientific papers
A selective, tin-free radical mediated synthesis of indoles based on a sulfonate template
Gray, Vincent James,Wilden, Jonathan D.
, p. 41 - 44 (2012)
A synthesis of indoles based on a vinyl sulfonate template is described. The approach employs a sulfonate group which plays three discrete roles in the synthetic sequence. Firstly the highly electron-withdrawing sulfonate group behaves as an activating group for a 1,4-addition of an aniline to the unsaturated system. Secondly, the electron-withdrawing nature of the same group also allows it to behave as a radical stabilising group which facilitates radical cyclisation to an aromatic ring to yield a transient indoline. Finally, the pendant sulfonate group behaves as a leaving group to yield the indole.
Tributyltin hydride and 1-ethylpiperidine hypophosphite mediated intermolecular radical additions to 2,4,6-trichlorophenyl vinyl sulfonate
Edetanlen-Elliot, Oluwabusola,Fitzmaurice, Richard J.,Wilden, Jonathan D.,Caddick, Stephen
, p. 8926 - 8929 (2007)
2,4,6-Trichlorophenyl vinyl sulfonate smoothly undergoes intermolecular radical addition under mild initiation conditions mediated by tributyltin hydride and 1-ethylpiperidine hypophosphite (EPHP) to generate a range of functionalised alkyl sulfonamide pr
Synthesis, bioconjugation and stability studies of [18F]ethenesulfonyl fluoride
Zhang, Bo,Pascali, Giancarlo,Wyatt, Naomi,Matesic, Lidia,Klenner, Mitchell A.,Sia, Tiffany R.,Guastella, Adam J.,Massi, Massimiliano,Robinson, Andrea J.,Fraser, Benjamin H.
, p. 847 - 856 (2018/08/03)
Fluorine-18 labelled prosthetic groups (PGs) are often necessary for radiolabelling sensitive biological molecules such as peptides and proteins. Several shortcomings, however, often diminish the final yield of radiotracer. In an attempt to provide higher yielding and operationally efficient tools for radiolabelling biological molecules, we describe herein the first radiochemical synthesis of [18F]ethenesulfonyl fluoride ([18F]ESF) and its Michael conjugation with amino acids and proteins. The synthesis of [18F]ESF was optimised using a microfluidic reactor under both carrier-added (c.a.) and no-carrier-added (n.c.a.) conditions, affording, in a straightforward procedure, 30-50% radiochemical yield (RCY) for c.a. [18F]ESF and 60-70% RCY for n.c.a. [18F]ESF. The conjugation reactions were performed at room temperature using 10?mg/mL precursor in aqueous/organic solvent mixtures for 15?min. The radiochemical stability of the final conjugates was evaluated in injectable formulation and rat serum, and resulted strongly substrate dependent and generally poor in rat serum. Therefore, in this work we have optimised a straightforward synthesis of [18F]ESF and its Michael conjugation with model compounds, without requiring chromatographic purification. However, given the general low stability of the final products, further studies will be required for improving conjugate stability, before assessing the use of this PG for PET imaging.
Synthesis of unsymmetrical ketones via simple C-H activation of aldehydes and concomitant hydroacylation of vinyl sulfonates
Fitzmaurice, Richard J.,Ahern, Jenna M.,Caddick, Stephen
supporting information; experimental part, p. 235 - 237 (2009/03/11)
A new and simple protocol for the direct functionalisation of aldehydes with concomitant conversion into ketones via C-C bond formation has been developed. The reaction effectively enables the direct C-H activation of an aldehyde by mixing of an aldehyde
