Catalytic N-diphosphonomethylation of amino alkanols and bisamino alkanes using tris(trimethylsilyl) phosphite as a convenient synthon.

• The new mono- and bis(aminomethylenediphosphonic) acids are synthesized in the presence of Me 3 SiOTf as a catalyst. • The catalytic schema of the resulting compounds syntheses include the formation of highly reactive iminium salts. • The target substances are structural analogues of well-known drugs and may be considered as promising polydentate ligands, antibacterial and antiviral compounds. The new mono- and bis(aminomethylenediphosphonic) acids are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N -formyl amino alkanols or bis(N -formyl amino) alkanes at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. The further treatment of initially formed trimethylsilyl intermediates with the methanol excess resulted in the crystalline mono- and bis(aminomethylenediphosphonic) acids in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target acids were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra (HRMS). The resulting compounds are of great interest as perspective bioactive substances with versatile properties and effective polydentate ligands. [Display omitted] [ABSTRACT FROM AUTHOR]