Development of a continuous process for alpha-thio-beta-chloroacrylamide synthesis with enhanced control of a cascade transformation

作者:Dennehy Olga C; Cacheux Valerie M Y; Deadman Benjamin J; Lynch Denis; Collins Stuart G*; Moynihan Humphrey A*; Maguire Anita R*
来源:Beilstein Journal of Organic Chemistry, 2016, 12: 2511-2522.
DOI:10.3762/bjoc.12.246

摘要

A continuous process strategy has been developed for the preparation of alpha-thio-beta-chloroacrylamides, a class of highly versatile synthetic intermediates. Flow platforms to generate the alpha-chloroamide and alpha-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 alpha-thio-beta-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 by products.

  • 出版日期2016-11-24