Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation

dc.contributor.authorDennehy, Olga C.
dc.contributor.authorCacheux, Valérie M. Y.
dc.contributor.authorDeadman, Benjamin J.
dc.contributor.authorLynch, Denis
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMoynihan, Humphrey A.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2016-12-09T09:40:45Z
dc.date.available2016-12-09T09:40:45Z
dc.date.issued2016-11-24
dc.date.updated2016-12-09T09:26:11Z
dc.description.abstractA continuous process strategy has been developed for the preparation of α-thio-β chloroacrylamides, a class of highly versatile synthetic intermediates. Flow platforms to generate the α-chloroamide and α-thioamide precursors were successfully adopted, progressing from the previously employed batch chemistry, and in both instances afford a readily scalable methodology. The implementation of the key α-thio-β-chloroacrylamide casade as a continuous flow reaction on a multi-gram scale is described, while the tuneable nature of the cascade, facilitated by continuous processing, is highlighted by selective generation of established intermediates and byproducts.en
dc.description.sponsorshipScience Foundation Ireland (grant: SFI SSPC2 12/RC/2275)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationDennehy, O. C., Cacheux, V. M. Y., Deadman, B. J., Lynch, D., Collins, S. G., Moynihan, H. A. and Maguire, A. R. (2016) ‘Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation’, Beilstein Journal Of Organic Chemistry, 12, pp. 2511-2522. doi:10.3762/bjoc.12.246en
dc.identifier.doi10.3762/bjoc.12.246
dc.identifier.endpage2522en
dc.identifier.issn1860-5397
dc.identifier.journaltitleBeilstein Journal Of Organic Chemistryen
dc.identifier.startpage2511en
dc.identifier.urihttps://hdl.handle.net/10468/3363
dc.identifier.volume12en
dc.language.isoenen
dc.publisherBeilstein-Instituten
dc.rights© 2016, Dennehy 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) The definitive version of this article is the electronic one which can be found at: doi:10.3762/bjoc.12.246en
dc.rights.urihttp://creativecommons.org/licenses/by/4.0en
dc.subjectCascade reactionsen
dc.subjectFlow chemistryen
dc.subjectα-thio-β-chloroacrylamidesen
dc.titleDevelopment of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformationen
dc.typeArticle (peer-reviewed)en
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