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

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. T...

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Bibliographic Details
Published in:Russian journal of general chemistry 2021-08, Vol.91 (8), p.1459-1465
Main Authors: Kolyamshin, O. A., Mitrasov, Yu. N., Danilov, V. A., Vasil’ev, A. N.
Format: Article
Language:English
Subjects:
Anti-arrhythmia drugs
Benzoates
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dimethylformamide
Hydantoin
Potassium
Substitution reactions
Type 2 diabetes
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Summary: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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363221080065