Beilstein J. Org. Chem.2019,15, 2864–2871, doi:10.3762/bjoc.15.280
biological evaluation, while their medicinal chemistry properties dramatically depend on the structure of the five-membered heterocyclic moiety and substituents in the C-5 position [7].
Some pseudothiohydantoins (2-iminothiazolidin-4-ones) are known to undergo a pseudothiohydantoin–thiohydantoin
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Graphical Abstract
Figure 1:
Hydantoin-based commercially available drugs.
Beilstein J. Org. Chem.2013,9, 689–697, doi:10.3762/bjoc.9.78
protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized
based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.
Keywords: 2-iminothiazolidin-4-ones; regioselective; stereoselective; solvent-free
; scavenger-free; Introduction
Thiazolidin-4-one derivatives are well known for their bioactivities such as antidiabetic [1], anticancer [2], calcium-channel blocker [3][4], platelet activating factor (PAF) antagonist [5] and anti-HIV [6] activity. In addition, 2-iminothiazolidin-4-ones exhibit remarkable