A general synthesis of previously unknown semicarbazone-based α-amidoalkylating reagents, 4-(tosylmethyl)semicarbazones, has been developed. The synthesis involved threecomponent condensation of semicarbazones of aliphatic or aromatic aldehydes with the same or other aldehydes and p-toluenesulfinic acid. The scope and limitations of this reaction were investigated. The compounds obtained were demonstrated to be an efficient α-4semicarbazono)alkylating agents. They were reacted with H-(sodium borohydride), O-(sodium methylate), S-(sodium phenylthiolate), N-(pyrrolidine, sodium succinimide), and P-nucleophiles (trialkyl phosphites) to give the corresponding products of the tosyl group substitution, 4substituted semicarbazones.