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• 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]

The new functionalized aminomethylenediphosphonates with moieties of various amino acids are synthesized via unique reaction of tris(trimethylsilyl) phosphite and N -formyl amino acids at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. The further treatment of aminomethylenediphosphonates with the methanol excess resulted in the water-soluble functionalized aminomethylenediphosphonic acids. [ABSTRACT FROM AUTHOR]

The new functionalized hydroxymethylphosphonic and methylenediphosphonic acids are synthesized via unique reaction of tris(trimethylsilyl) phosphite and N -formyl N -heterocycles, N-substituted 4-piperidones, 3-quinuclidone, and 2-adamantanone at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. [ABSTRACT FROM AUTHOR]

• The new methylenediphosphonates with non-proteinogenic amino acid and aminosulfonic acid moieties 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 non-proteinogenic amino acids with methylenebisphosphonic acids moieties are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N -formyl amino acids 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 water-soluble non-proteinogenic amino acids with methylenebisphosphonic acids moieties in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target functionalized amino acids and their precursors were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra. The resulted compounds are of great interest as promising antiviral substances and effective ligands. [Display omitted] [ABSTRACT FROM AUTHOR]

The convenient silicon-assisted synthesis of new aminomethylenebisphosphonic acids and their precursors was developed via unique methodology. So new aminomethylenebisphosphonic acids with quinolines moieties were obtained using suitable reaction of tris(trimethylsilyl) phosphite and N -formyl aminoquinolines catalyzed by trimethylsilyl triflate under mild conditions (20 °C). The initially formed intermediates – tetra (trimethylsilyl) aminomethylenebisphosphonates are transformed to target acids by methanolysis in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of aminomethylenebisphosphonic acids and their precursors with substituted quinoline moieties were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra. Image 1 • The new quinolyl aminomethylenediphosphonates are synthesized in the presence of Me 3 SiOTf as a catalyst. • The resulting substances are structural analogues of well-known drugs and may be considered as promising polydentate ligands and plant growth regulating agents. [ABSTRACT FROM AUTHOR]

The new convenient synthesis of functionalized aryl and pyridyl aminomethylenebisphosphonic acids and their derivatives has been developed via silicon-assisted methodology. New functionalized aminomethylenebisphosphonic acids containing pyridines moieties were obtained using unique reaction of tris(trimethylsilyl) phosphite with N -formyl aminopyridines and trimethylsilyl triflate as a catalyst under mild conditions. Intermediates – tetra(trimethylsilyl) aminomethylenebisphosphonates formed, were converted to the target acids by further treatment with methanol excess. In contrast the corresponding tetraethyl aminomethylenebisphosphonates were synthesized under heating (130 °C) of four component mixture (diethyl trimethylsilyl phosphite, triethyl orthoformate, aryl- or pyridylamine, and diethyl phosphite) in the presence of zinc chloride catalyst. The catalytic schemes of target substances formation are proposed and thoroughly discussed. Image 1 • The new aryl and pyridyl aminomethylenediphosphonates are synthesized in the presence of Me 3 SiOTf or ZnCl 2 as catalysts.. • The catalytic schemes of the target compounds synthesis include the formation of highly reactive iminium salts. • The resulting substances are structural analogues of well-known drugs and may be considered as promising polydentate ligands. [ABSTRACT FROM AUTHOR]