A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

Arno Verlee; Thomas Heugebaert; Tom van der Meer; Pavel I Kerchev; Frank Van Breusegem; Christian V Stevens

doi:10.3762/bjoc.13.33

A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

Beilstein J Org Chem. 2017 Feb 16:13:303-312. doi: 10.3762/bjoc.13.33. eCollection 2017.

Authors

Arno Verlee¹, Thomas Heugebaert¹, Tom van der Meer², Pavel I Kerchev², Frank Van Breusegem², Christian V Stevens¹

Affiliations

¹ Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Campus Coupure, Coupure Links 653, B-9000 Ghent, Belgium.
² Department of Plant Systems Biology, VIB, Ghent University, Technologiepark 927, B-9000 Ghent, Belgium; Department of Plant Biotechnology and Bioinformatics, Ghent University, Technologiepark 927, B-9052 Ghent, Belgium.

Abstract

For the synthesis of m-sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from m-(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process reveals an increased selectivity at higher temperatures and without catalysts. In total, 15 analogues were synthesized, using similar conditions, with yields ranging between 65 and 99%. This is the first automated and chemoselective synthesis of m-sulfamoylbenzamide analogues.

Keywords: flow chemistry; m-sulfamoylbenzamide analogues; medium-throughput synthesis.