Reactions with 5-Arylazo- and 5-Arylidene-4-thiohydantoin Derivatives

Abstract

5-Arylazo-3-phenyl-4-thiohydantoins (IIa-g) have been prepared and then treated with primary aromatic amines to afford the corresponding 5-arylazo-4-arylimino-3-phenyl hydantoins (VIIa-c). 3-Phenyl-4-thiohydantoin reacted with aromatic aldehydes in the presence of glacial acetic acid and fused sodium acetate to give 5-arylidene-3-phenyl-4-thiohydantoin derivatives (VIIIa-e). In the coloured arylidene derivatives (VIII,a d, e) on treatment with alkyland/ or arylmagnesium halide addition occurs to the exocyclic double bond to give the products (IXa-e). The Grignard product (Xa) was oxidised with a mixture of chromic acid in glacial acetic acid to give phenyl parabanic acid and ethyl phenyl ketone

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