Beilstein J. Org. Chem.2016,12, 2511–2522, doi:10.3762/bjoc.12.246
-chloroacrylamides; cascade reactions; flow chemistry; Introduction
Since the efficient and highly stereoselective transformation of α-thioamides to the corresponding α-thio-β-chloroacrylamides derivatives was first reported [1][2], the considerable synthetic utility of these heavily functionalized acrylamide
ready access to appreciable quantities of material is required. Preparation of α-thio-β-chloroacrylamides typically results from a three-step synthetic route, culminating in a final cascade/domino reaction [13] where a toluene solution of α-thioamide and NCS is subjected to a ‘hot plunge’ by placing it
envisaged that continuous processing could facilitate the preparation of large quantities of α-thio-β-chloroacrylamide with reduced purification requirements. The goal of this study was to develop an optimized process for the synthesis of α-thio-β-chloroacrylamides, employing a model system with N-4
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Graphical Abstract
Scheme 1:
Reaction pathways of α-thio-β-chloroacrylamides.