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Phosphorylation of Benzimidazole-2-thiones by Chloroethynylphosphonate

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Abstract

The reaction of chloroethynylphosphonates with N-substituted benzimidazole-2-thiones proceeded chemo- and regioselectively with the formation of cyclic zwitterions, namely alkyl (9H-benzo[4,5]imidazo[2,1-b]-thiazol-3-yl-4-ium)phosphonates. Chemo- and regioselective reaction of N-unsubstituted benzimidazole-2-thione with chloroethynylphosphonates led to the production of linear Z-1,2-bis(1H-benzimidazol-2-ylsulfanyl)-ethenylphosphonates.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    D. M. Egorov, Yu. L. Piterskaya, D. D. Kartsev, M. N. Krivchun & A. V. Dogadina

  2. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. D. M. Egorov
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  2. Yu. L. Piterskaya
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  3. D. D. Kartsev
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  4. V. A. Polukeev
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  5. M. N. Krivchun
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  6. A. V. Dogadina
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Correspondence to A. V. Dogadina.

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Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © D.M. Egorov, Yu.L. Piterskaya, D.D. Kartsev, V.A. Polukeev, M.N. Krivchun, A.V. Dogadina, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1478–1485.

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Egorov, D.M., Piterskaya, Y.L., Kartsev, D.D. et al. Phosphorylation of Benzimidazole-2-thiones by Chloroethynylphosphonate. Russ J Gen Chem 88, 1824–1831 (2018). https://doi.org/10.1134/S1070363218090104

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  • DOI: https://doi.org/10.1134/S1070363218090104

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