Synthesis and some transformations of dimethyl anabasylethynephosphonate

A new phosphorylated ynamine, dimethyl anabasylethynephosphonate, was synthesized by reaction of dimethyl chloroacetylenephosphonate with anabasine. Anabasylethynephosphonate obtained was shown to react under mild conditions with primary aromatic amines like p-chloroaniline, p-anisidine, and p-aminoacetophenone, whose pK _b values are in the range of 9–13, to form new asymmetrical phosphorylated acetamidines in high yields. Structure of the compounds obtained was proved by ¹H, ¹³C, and ³¹P NMR spectroscopy.