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Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N!C triad were revealed and applied in the synthesis of =-aminophosphonic acid derivatives.Imidoylphosphonates containing a-hydrogen atoms in the N-alkyl group are potential 1,3-prototropic systems. Prototropy the phosphorylated C=N3C 1,3-prototropic triad presents both theoretical and practical interest. The A 76 47 B interconversion can be regarded as a [phosphorus] model of the biochemical transamination reaction in living bodies.The 1,3-prototropic shift in the phosphorylated azaallyl triad makes evident genetic relation between derivatives of imidoylphosphonic (A) and a-aminoalkylphosphonic acids (B) that attract increased interest in view of their biological activity [2, 3].Transformations like A 6 B belong to fundamental properties of imidoylphosphonates and form an important method for preparing a-aminoalkylphosphoryl derivatives [4].In previous communications of this series we showed that the phosphorus-containing group controls facility and direction of prototropic migrations in the C=N3C triad. In detail it was established [4,5] that N-benzylbenzimidoylphosphoryl derivatives I under mild conditions, even in the absence of bases, undergo an irreversible 1,3-prototropic shift to form Nbenzylidene-a-aminoalkylphosphoryl derivatives II (Scheme 1).To assess the effect of the N-alkyl substituent on the prototropy in the C3N3C triad, in the present work ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communication XIX, see [1]. Scheme 1.; C 9 0 P ; 9 0 P = T

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ChemInform Abstract The title compounds (III) are prepared by condensation reaction of the acylphosphonates (I) with the α-aminoalkylphosphonates (II) in the presence of p-toluenesulfonic acid.