Fluorous synthesis of hydantoins and thiohydantoins.
[reaction: see text] A fluorous synthesis of hydantoins is introduced. The reaction of perfluoroalkyl (Rfh)-tagged amino esters with an isocyanate is followed by the cyclization of ureas and simultaneous cleavage of the fluorous tag to afford hydantoins. The product purification is performed by solid-phase extraction over FluoroFlash cartridges, and no fluorous solvent is involved in either the reaction or the separation processes. The same method applies to synthesis of thiohydantoins.
Zhang
Wei
W
Fluorous Technologies, Inc., University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA. w.zhang@fluorous.com
Lu
Yimin
Y
D006827:Hydantoins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013867:Thiohydantoins / Q000737:chemistry*
D006827:Hydantoins; D013867:Thiohydantoins