Title: α-Amino acetals containing a phosphonate or phosphine oxide group. Synthesis and reactions with resorcinols.
Authors: Vagapova, L.; Amirova, L.; Pavlova, E.; Burilov, A.; Voronina, Yu.; Syakaev, V.; Sharafutdinova, D.; Rizvanov, I.; Garifzyanov, A.; Pudovik, M.
Abstract: New α-amino acetals containing a phosphonate or phosphine oxide group were synthesized by the Kabachnik-Fields reaction in the ternary system amino acetal-paraformaldehyde-dialkyl phosphonate (or dialkylphosphine oxide). Condensation of dialkyl (2,2-dimethoxyethylamino)methylphosphonates with resorcinol and its derivatives in ethanol in the presence of hydrochloric acid, apart from the corresponding 2,2-bis(polyhydroxyphenyl) ethylammonium salts, gave 2,5-bis(polyhydroxyphenyl)-1,4-bis[(dialkoxyphosphoryl)methyl]-piperazines. Dialkyl[(2,2-dimethoxyethylamino)methyl]phosphine oxides (Alk = CH, CH) did not react with resorcinol derivatives under similar conditions, and analogous ammonium salts were obtained by heating the reactants in boiling trifluoroacetic acid.
Subjects: PHENOLS; PHOSPHINE; PHOSPHORUS compounds; PHOSPHINES; PHOSPHINE oxides
Publication: Russian Journal of Organic Chemistry, 2014, Vol 50, Issue 4, p469
ISSN: 1070-4280
Publication type: Academic Journal
DOI: 10.1134/S1070428014040034

α-Amino acetals containing a phosphonate or phosphine oxide group. Synthesis and reactions with resorcinols.

Vagapova, L.; Amirova, L.; Pavlova, E.; Burilov, A.; Voronina, Yu.; Syakaev, V.; Sharafutdinova, D.; Rizvanov, I.; Garifzyanov, A.; Pudovik, M.