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Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles

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Abstract

A series of new 6-phosphonylated 1H-imidazo[2,1-c][1,2,4]triazoles was synthesized by the reaction of diethyl chloroethynylphosphonate with 2-substituted 3-amino-1,2,4-triazoles followed by 5-endo-dig cyclization. It was found that 3-amino-5-bromo-1,2,4-triazole reacts in another way, leading to the formation of the corresponding symmetric amidine, diethyl {2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)amino]-2-[(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)imino]ethyl}phosphonate.

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Funding

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (project no. 785.00.X6019) and the Russian Foundation for Basic Research (grant no. 19-03-00365) using the equipment of the Engineering Center of the St. Petersburg State Institute of Technology, and Resource Centers “Center for X-Ray Diffraction Studies” and “Chemical Analysis and Materials Research Center” of the Research Park of St. Petersburg State University.

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Authors and Affiliations

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

    A. S. Krylov, V. V. Tolstyakov & A. V. Dogadina

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

    V. V. Gurzhiy

Authors
  1. A. S. Krylov
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  2. V. V. Tolstyakov
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  3. V. V. Gurzhiy
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  4. A. V. Dogadina
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Correspondence to A. V. Dogadina.

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Krylov, A.S., Tolstyakov, V.V., Gurzhiy, V.V. et al. Reaction of Diethyl Chloroethynylphosphonate with 3-Amino-1,2,4-triazoles. Russ J Gen Chem 91, 72–76 (2021). https://doi.org/10.1134/S1070363221010072

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