Abstract
N-aminorhodanine reacts with ethyl chlorooxoacetate in ethanol to produce ethyl N-(4-oxo-2-thioxothiazolidin-3-yl)oxalamate in nearly quantitative yield. Reaction between this adduct and electron-deficient acetylenic esters in the presence of triphenylphosphine leads to dialkyl 4-ethoxy-5-oxo-1-(4-oxo-2-thioxothiazolidin-3-yl)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate derivatives in good yields.
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