Synthesis of thiazolidin-4-ones from α-enolic dithioesters and α-halohydroxamates

A facile access to thiazolidin-4-ones from alpha-enolic dithioesters and alpha-halohydroxamates in situ derived active 1,3-dipolar aza-oxyallyl cations was achieved under mild conditions. These five-membered heterocycles with Z-exocyclic double bonds and diverse substituents can be readily obtained via a regio- and stereoselective formal [3+2] cycloaddition pathway.

Automated summary

Thiazolidin-4-ones were successfully synthesized from alpha-enolic dithioesters and alpha-halohydroxamates via active 1,3-dipolar aza-oxyallyl cations, resulting in five-membered heterocycles with Z-exocyclic double bonds and diverse substituents. This synthetic pathway demonstrates regio- and stereoselectivity in achieving the desired products through a formal [3+2] cycloaddition approach.