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Beilstein J. Org. Chem. 2019, 15, 2864–2871, doi:10.3762/bjoc.15.280
Graphical Abstract
Figure 1: Hydantoin-based commercially available drugs.
Scheme 1: Pseudothiohydantoin–thiohydantoin rearrangement.
Scheme 2: Syntheses of regioisomeric 5-spiro-substituted thiohydantoins and pseudothiohydantoins: previous [10] a...
Figure 2: Electrophilic centers of FPDs 1, starting materials of this study.
Scheme 3: Cyclocondensation of FPDs 1 with 1,3-binucleophilic reagents, resulting in pyrrole-2-one-bearing sp...
Scheme 4: Reaction of FPD 1a with thiourea.
Scheme 5: PTR of 3a to 2a.
Scheme 6: Pathways for the formation of compound 2a.
Scheme 7: Reaction of FPD 1a with monosubstituted thioureas.
Scheme 8: Reaction of FPDs 1 with 1,3-dibutylthiourea at room temperature.
Scheme 9: Plausible PTR pathways.