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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.

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill Thumbnail


Authors

Olga Eguaogie

Patrick F. Conlon

Francesco Ravalico

Jamie S.T. Sweet

Thomas B. Elder

Louis P. Conway

Marc E. Lennon

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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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

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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