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Some Features of Nucleophilic Substitution Reactions of N-2-Haloethyl Derivatives of 5,5-Substituted Hydantoins

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Abstract

Reaction of 5,5-dimethyl-3-(2-chloroethyl)- and 5,5-diphenyl-3-(2-bromoethyl)- hydantoins with potassium 4-aminobenzoate in dimethylformamide in the presence of triethylbenzylammonium chloride leads to the formation of 2-[5,5-dimethyl(diphenyl)-2,4-dioxo-1,3-diazolidin-2-yl]ethyl-4-aminobenzoates. The latter were used for synthesis of new types of maleimides, namely 2-[5,5-dimethyl(diphenyl)-2,4-dioxo-1,3-diazolidin-2-yl]ethyl-4-(2,5-dioxo-1-azolin-1-yl) benzoates. Reactions of 5,5-dimethyl-1,3-di(2-chloroethyl) hydantoin with potassium 4-aminobenzoate or sodium 4-N-acetylaminophenolate at a molar ratio of 1:2 also lead to 3-monosubstituted products.

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Authors and Affiliations

  1. I.N. Ulyanov Chuvash State University, 428015, Cheboksary, Russia

    O. A. Kolyamshin, V. A. Danilov & A. N. Vasil’ev

  2. I.Ya. Yakovlev Chuvash State Pedagogical University, 428000, Cheboksary, Russia

    Yu. N. Mitrasov

Authors
  1. O. A. Kolyamshin
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  2. Yu. N. Mitrasov
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  3. V. A. Danilov
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  4. A. N. Vasil’ev
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Correspondence to O. A. Kolyamshin.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 8, pp. 1184–1191 https://doi.org/10.31857/S0044460X21080060.

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Kolyamshin, O.A., Mitrasov, Y.N., Danilov, V.A. et al. Some Features of Nucleophilic Substitution Reactions of N-2-Haloethyl Derivatives of 5,5-Substituted Hydantoins. Russ J Gen Chem 91, 1459–1465 (2021). https://doi.org/10.1134/S1070363221080065

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