title: Three-component, one-flask synthesis of rhodanines (thiazolidinones).
abstract: 5-(Z)-alkylidene-2-thioxo-1,3-thiazolidin-4-ones (rhodanine derivatives) were prepared by reaction of in situ generated dithiocarbamates with recently reported racemic α-chloro-β,γ-alkenoate esters. This multicomponent sequential transformation performed in one reaction flask represents a general route to this medicinally valuable class of sulfur/nitrogen heterocycles. Using this convergent procedure, we prepared an analogue of the drug epalrestat, an aldose reductase inhibitory rhodanine.
authors.affiliation: Department of Chemistry, The Johns Hopkins University, 3400 N. Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Jacobine
authors.forename: Gary H
authors.initials: GH
authors.lastname: Posner
mesh_terms: D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D012236:Rhodanine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004791:Enzyme Inhibitors; D012236:Rhodanine; D000449:Aldehyde Reductase