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Reactions of 4,5-Dimethylimidazole-2-thione and Benzimidazole-2-thione with Dialkyl Chloroethynylphosphonates in the Presence of Potassium Carbonate

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Abstract

The reactions of dialkyl chloroethynylphosphonates with substituted imidazole-2-thiones and benzimidazole-2-thione in anhydrous acetonitrile occurs selectively with the formation of alkenephosphonates. Similar reactions in the presence of an equimolar amount of anhydrous K2CO3 unexpectedly leads to the formation of fused cyclic phosphonates, namely dialkyl {5,6-dimethyl(benzo)imidazo[2,1-b]thiazol-3-yl}phosphonates in high yields.

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Funding

This work was carried out within the framework of the basic part of the governmental task of the Ministry of Science and Higher Education (no. 785.00.X6019) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology. The work was financially supported by the Russian Foundation for Basic Research (grant no. 18-33-00430).

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Authors and Affiliations

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

    A. A. Babushkina, D. M. Egorov, Yu. L. Piterskaya & V. S. Zavgorodnii

  2. St. Petersburg State University, 199034, St. Petersburg, Russia

    D. D. Kartsev

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  1. A. A. Babushkina
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  2. D. M. Egorov
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  3. D. D. Kartsev
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  4. Yu. L. Piterskaya
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Correspondence to A. A. Babushkina.

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Babushkina, A.A., Egorov, D.M., Kartsev, D.D. et al. Reactions of 4,5-Dimethylimidazole-2-thione and Benzimidazole-2-thione with Dialkyl Chloroethynylphosphonates in the Presence of Potassium Carbonate. Russ J Gen Chem 90, 1197–1201 (2020). https://doi.org/10.1134/S107036322007004X

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