Some chemical transformations of alkyl (4-aminophenyl)carbamates

Azo coupling of diazonium salts derived from alkyl (4-aminophenyl)carbamates with ethyl α-methylacetoacetate gave ethyl 5-alkoxycarbonylamino-1H-indole-2-carboxylates. The condensation of aminophenylcarbamates with aromatic aldehydes in ethanol afforded the corresponding Schiff bases. Cyclohexyl {4-(4-methoxyphenyl)methylidene]aminophenyl}carbamate reacted with chloroacetyl chloride in dioxane in the presence of triethylamine to produce cyclohexyl {4-3-chloro-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]phenylcarbamate, and the reaction of benzyl {4-(4-nitrophenyl)methylidene]aminophenyl}carbamate with sulfanylacetic acid in DMF led to the formation of benzyl {4-2-(4-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]-phenyl}carbamate.