Synthesis of functionalized mono-, bis-, and tris(spirophosphoranyl) amines and amino acids

Abstract

Convenient syntheses of functionalized PCH₂N-containing mono-, bis-, and tris-(spirophosphoranylmethyl)amines and analogous amino acids based on hydrospirophosphoranes of the 1,4,6,9-tetraoxa-5λ⁵-phosphaspiro[4.4]nonane type using mono-, bis-, and tris-aminomethylating agents have been developed. Transesterification of diethyl esters of N,N-disubstituted aminomethylphosphonous acids with ethylene glycol is accompanied by a redox process and furnishes aminomethylspirophosphoranes. The target compounds are of interest as biologically active substances, polydentate chelating ligands, and also as promising monomers for the synthesis of phosphorus-containing polymers.