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

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

Dennehy, Olga C.; Cacheux, Valérie M. Y.; Deadman, Benjamin J.; Lynch, Denis; Collins, Stuart G.; Moynihan, Humphrey A.; Maguire, Anita R.
Date: 2016-11-24
Copyright: © 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
Copyright information: http://creativecommons.org/licenses/by/4.0
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
Published Version: 10.3762/bjoc.12.246

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.

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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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