Reactions with 5‐substituted 4‐arylimino‐2‐thiazolidinones

Abstract

AbstractThe reaction of 5‐arylidene‐4‐arylimino‐2‐thiazolidinones 4 with GRIGNARD reagents effected 1,4‐addition to the exocyclic CC bond with the formation of 5. Alkylation of the arylidene derivatives 4 with diazomethane or methyl iodide results in the formation of the N‐methyl derivatives 6. Treatment of 6 with phenylmagnesium bromide effects addition of the reagent to the double bond of the lateral chain to yield products, proved to have structure 8.The 5‐arylazo derivatives 9 of 4‐arylimino‐2‐thiazolidinones were obtained by coupling 4 with aromatic diazonium chlorides. Compounds 9 were N‐methylated with diazomethane to yield 10.