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Synthesis and some transformations of dimethyl anabasylethynephosphonate

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Abstract

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.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    N. I. Svintsitskaya, A. V. Dogadina & B. I. Ionin

  2. Sh. Ualikhanov Kokshetau State University, ul. Abaya, 76, Kokshetau, 020000, Kazakhstan

    O. A. Aimakov

Authors
  1. N. I. Svintsitskaya
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  2. O. A. Aimakov
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  3. A. V. Dogadina
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  4. B. I. Ionin
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Correspondence to N. I. Svintsitskaya.

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Original Russian Text © N.I. Svintsitskaya, O.A. Aimakov, A.V. Dogadina, B.I. Ionin, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 7, pp. 1104–1109.

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Svintsitskaya, N.I., Aimakov, O.A., Dogadina, A.V. et al. Synthesis and some transformations of dimethyl anabasylethynephosphonate. Russ J Gen Chem 79, 1461–1466 (2009). https://doi.org/10.1134/S1070363209070093

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  • DOI: https://doi.org/10.1134/S1070363209070093

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