Olga Eguaogie
Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Eguaogie, Olga; Conlon, Patrick F.; Ravalico, Francesco; Sweet, Jamie S.T.; Elder, Thomas B.; Conway, Louis P.; Lennon, Marc E.; Hodgson, David R.W.; Vyle, Joseph S.
Authors
Patrick F. Conlon
Francesco Ravalico
Jamie S.T. Sweet
Thomas B. Elder
Louis P. Conway
Marc E. Lennon
Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor
Joseph S. Vyle
Abstract
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.
Citation
Eguaogie, O., Conlon, P. F., Ravalico, F., Sweet, J. S., Elder, T. B., Conway, L. P., …Vyle, J. S. (2017). Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill. Beilstein Journal of Organic Chemistry, 13, 87-92. https://doi.org/10.3762/bjoc.13.11
Journal Article Type | Article |
---|---|
Acceptance Date | Dec 30, 2016 |
Online Publication Date | Jan 13, 2017 |
Publication Date | Jan 13, 2017 |
Deposit Date | Jan 3, 2017 |
Publicly Available Date | Jan 16, 2017 |
Journal | Beilstein Journal of Organic Chemistry |
Print ISSN | 1860-5397 |
Publisher | Beilstein-Institut |
Peer Reviewed | Peer Reviewed |
Volume | 13 |
Pages | 87-92 |
DOI | https://doi.org/10.3762/bjoc.13.11 |
Public URL | https://durham-repository.worktribe.com/output/1389377 |
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Copyright Statement
© 2017 Eguaogie et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
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