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Phosphorylated 2-Chloroethynes in the Reactions with Malonic Acid Derivatives: Azirine or Oxazole?

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Abstract

The reactions of (2-chloroethynyl)diphenylphosphine oxide with diethyl 2-aminomalonate and of dimethyl (2-chloroethynyl)phosphonate with 2-amino-N1,N3-di(p-tolyl)malonamide or 2-aminomalonamide proceed chemo- and regioselectively to yield the corresponding 2-(phosphorylmethylene)oxazoles, namely diphenyl-[(4-ethoxycarbonyl-5-ethoxyoxazol-2-yl)methyl]phosphine oxide, dimethyl {[5-(p-tolylamino)-4-(p-tolylcarbamoyl)oxazol-2-yl]methyl}phosphonate, and dimethyl [(5-amino-4-carbamoyloxazol-2-yl)methyl]phosphonate, respectively.

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Funding

This study was performed in the scope of the basic part of the State Task of the Ministry of Education and Science of the Russian Federation (no. 785.00.Х6019) using the equipment of the Engineering Center of St. Petersburg State Institute of Technology and Resource Centers “X-ray Diffraction Methods” and “Methods of Analysis of Composition” of Science Park of St. Petersburg State University, with financial support from Russian Foundation for Basic Research (grant no. 19-03-00365).

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Authors and Affiliations

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

    N. B. Viktorov & A. V. Dogadina

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

    V. V. Gurzhiy

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  1. N. B. Viktorov
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  2. V. V. Gurzhiy
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  3. A. V. Dogadina
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Correspondence to A. V. Dogadina.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1059–1067 https://doi.org/10.31857/S0044460X21070106.

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Viktorov, N.B., Gurzhiy, V.V. & Dogadina, A.V. Phosphorylated 2-Chloroethynes in the Reactions with Malonic Acid Derivatives: Azirine or Oxazole?. Russ J Gen Chem 91, 1325–1332 (2021). https://doi.org/10.1134/S1070363221070100

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