Direct Access to 2‐Thioxooxazolidin‐4‐ones and Oxazolidine‐2,4‐diones from α‐Keto Thioesters through Thiolate Transfer

Abstract

Abstract We report a direct synthesis of 2‐thioxooxazolidin‐4‐ones and oxazolidine‐2,4‐diones from α‐keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization. magnified image