Novel semicarbazone-based α-amidoalkylating reagents: general synthesis and reactions with H-, O-, S-, N-, and P-nucleophiles

A general synthesis of previously unknown semicarbazone-based α-amidoalkylating reagents, 4-(tosylmethyl)semicarbazones, has been developed. The synthesis involved three-component 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-4-semicarbazono)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, 4-substituted semicarbazones.