Expedient Lewis acid catalyzed synthesis of a 3-substituted 5-arylidene-1-methyl-2-thiohydantoin Library.
An efficient and rapid solution phase combinatorial synthesis of a 3-substituted 5-arylidene-1-methyl-2-thiohydantoin library was developed. The salient feature for this library production procedure is the addition of the Lewis acid catalyst, indium(III) trifluoromethanesulfonate, which serves to facilitate the direct condensation of aldehydes with 3-substituted 1-methyl-2-thiohydantoins. Use of this Lewis acid catalyst has resulted in faster reaction times, higher conversions and better purity profiles for these condensation reactions as compared to traditional uncatalyzed reactions. The resulting 315 member library of 3-substituted 5-arylidene-1-methyl-2-thiohydantoin is described.
Gregg
Brian T
BT
Department of Medical Chemistry, AMRI, 26 Corporate Circle, Albany, New York 12203, USA. brian.gregg@amriglobal.com
Golden
Kathryn C
KC
Quinn
John F
JF
Tymoshenko
Dmytro O
DO
Earley
William G
WG
Maynard
Dacia A
DA
Razzano
Dana A
DA
Rennells
W Martin
WM
Butcher
Jennifer
J
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D013867:Thiohydantoins / Q000138:chemical synthesis*
D000447:Aldehydes; C522942:Indium(III) trifluoromethanesulfonate; D009942:Organometallic Compounds; D013867:Thiohydantoins