Russian Journal of General Chemistry

, Volume 88, Issue 3, pp 439–451 | Cite as

Aminophosphonocarboxylates of the Furan Series

  • L. M. Pevzner
  • V. S. Zavgorodnii


Halomethyl derivatives of (diethoxyphosphorylmethyl)furan-2(3)-carboxylates containing blocking methyl group in the position 5 of the furan ring were synthesized. In the course of constructing of carbon skeleton of these compounds it was found that alkyl 3-methoxymethyl-, 3-chloromethyl-, and 3-(diethoxyphosphorylmethyl)-5-methyl-2-furoates are halomethylated at elevated temperature in the position 4 of the furan ring. No ring destructure or transformation of the side chain of substituents was observed. The obtained halomethylfurans and their tert-butyl analogs by treating with sodium azide in acetonitrile were converted to corresponding azides. The reduction of latter with triphenylphosphine in ethanol led to formerly unavailable aminophosphonocarboxylates of the furan series.


furans halomethylation of furans chloromethylfuroic acids reduction with triphenylphosphine aminophosphonocarboxylic acids 


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  1. 1.
    Pevzner, L.M., Russ. J. Gen. Chem., 2017, vol. 87, no. 11, p. 2563. doi 10.1134/S1070363217110093CrossRefGoogle Scholar
  2. 2.
    Brucoli, A., Notoli, A., Marimuthu, P., Botello, M.T., Stapleton, P., Gibbons, S., and Schatzlein, A., Bioorg. Med. Chem., 2012, vol. 20, p. 2019. doi 10.1016/jbmc2012.01.043CrossRefGoogle Scholar
  3. 3.
    Pevzner, L.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 3, p. 404. doi 10.1134/S1070363212030073CrossRefGoogle Scholar
  4. 4.
    Pevzner, L.M., Ignat’ev, V.M., and Ionin, B.I., Russ. J. Gen. Chem., 1994, vol. 84, no. 12, p. 1754.Google Scholar
  5. 5.
    Pevzner, L.M., Russ. J. Gen. Chem., 2003, vol. 73, no. 12, p. 1877. doi 10.1123/B:RUGC.0000025146.10575.79CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia

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