Phosphorylation of Benzimidazole-2-thiones by Chloroethynylphosphonate

D. M. Egorov; Yu. L. Piterskaya; D. D. Kartsev; V. A. Polukeev; M. N. Krivchun; A. V. Dogadina

doi:10.1134/S1070363218090104

Phosphorylation of Benzimidazole-2-thiones by Chloroethynylphosphonate

Authors: Egorov D.M.¹, Piterskaya Y.L.¹, Kartsev D.D.¹, Polukeev V.A.², Krivchun M.N.¹, Dogadina A.V.¹
Affiliations:
1. St. Petersburg State Institute of Technology (Technical University)
2. Institute of Experimental Medicine
Issue: Vol 88, No 9 (2018)
Pages: 1824-1831
Section: Article
URL: https://journals.rcsi.science/1070-3632/article/view/222407
DOI: https://doi.org/10.1134/S1070363218090104
ID: 222407

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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.