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

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dc.contributor.author Dennehy, Olga C.
dc.contributor.author Cacheux, Valérie M. Y.
dc.contributor.author Deadman, Benjamin J.
dc.contributor.author Lynch, Denis
dc.contributor.author Collins, Stuart G.
dc.contributor.author Moynihan, Humphrey A.
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2016-12-09T09:40:45Z
dc.date.available 2016-12-09T09:40:45Z
dc.date.issued 2016-11-24
dc.identifier.citation Dennehy, 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.12.246 en
dc.identifier.volume 12 en
dc.identifier.startpage 2511 en
dc.identifier.endpage 2522 en
dc.identifier.issn 1860-5397
dc.identifier.uri http://hdl.handle.net/10468/3363
dc.identifier.doi 10.3762/bjoc.12.246
dc.description.abstract A 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.sponsorship Science Foundation Ireland (grant: SFI SSPC2 12/RC/2275) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Beilstein-Institut en
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.12.246 en
dc.rights.uri http://creativecommons.org/licenses/by/4.0 en
dc.subject Cascade reactions en
dc.subject Flow chemistry en
dc.subject α-thio-β-chloroacrylamides en
dc.title Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2016-12-09T09:26:11Z
dc.description.version Published Version en
dc.internal.rssid 375019486
dc.contributor.funder Science Foundation Ireland en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Beilstein Journal Of Organic Chemistry en
dc.internal.copyrightchecked Yes en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress a.maguire@ucc.ie en


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© 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.12.246 Except where otherwise noted, this item's license is described as © 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.12.246
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