Imine-based synthesis of functionalized phosphorus-containing carboxamides

Convenient syntheses of functionalized phosphorus-containing carboxamides based on the reaction of adducts of imines and carboxylic acid chlorides with trimethylsilyl esters of trivalent phosphorus acids have been developed. Adducts ClCH(Ar)—N(R)C(O)R′ are convenient synthons for the preparation of the target phosphorus-containing carboxamides bearing P(O)—C—N—C(O) moieties. The resulting compounds contain polar amide and phosphoryl moieties, have potential biological activity, and are also of interest as effective extractants and polydentate chelating ligands.