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.

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

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Published Version

Date

2016-11-24

Authors

Dennehy, Olga C.

Cacheux, Valérie M. Y.

Deadman, Benjamin J.

Lynch, Denis

Collins, Stuart G.

Moynihan, Humphrey A.

Maguire, Anita R.

Publisher

Beilstein-Institut

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.

Keywords

Cascade reactions , Flow chemistry , α-thio-β-chloroacrylamides

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