A chemoselective and continuous synthesis of m -sulfamoylbenzamide analogues

For the synthesis of sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from -(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process reveals...

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Veröffentlicht in:Beilstein journal of organic chemistry 2017-02, Vol.13 (1), p.303-312
Hauptverfasser: Verlee, Arno, Heugebaert, Thomas, van der Meer, Tom, Kerchev, Pavel I, Van Breusegem, Frank, Stevens, Christian V
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Sprache:eng
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Zusammenfassung:For the synthesis of sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from -(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 -sulfamoylbenzamide analogues.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.13.33