An efficient pathway for the selective preparation of monopropargyl-substituted
phosphonocarboxylate (PC) has been developed via the addition of
sodium acetylenide to ethylidenephosphonate. The reaction works
perfectly on multi-gram scales. The synthesis of the corresponding
methyl(propargyl)-, trifluoromethyl(propargyl)-, and dipropargyl-substituted
derivatives was elaborated based on direct alkylation of either
the correspondingly substituted phosphonocarboxylates or methylene
phosphonocarboxylate with excess of propargyl bromide. A series
of novel potentially biologically active 1,2,3-triazole-containing
phosphono-carboxylates were synthesized using copper(I)-catalysed
1,3-dipolar cycloaddition of organic azides with propargyl-substituted phosphonocarboxylates.
phosphonocarboxylates - ethylidenephosphonate - alkylation - sodium acetylenide - 1,3-dipolar cycloaddition - azides - phosphorylated 1,2,3-triazoles
