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

• Published in: Russian journal of general chemistry Vol. 91; no. 8; pp. 1459 - 1465
• Main Authors: Kolyamshin, O. A., Mitrasov, Yu. N., Danilov, V. A., Vasil’ev, A. N.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.08.2021; Springer Nature; Springer; Springer Nature B.V
• Subjects: Anti-arrhythmia drugs; Benzoates; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Dimethylformamide; Hydantoin; Physical Sciences; Potassium; Science & Technology; Substitution reactions; Type 2 diabetes; 5,5-dimethyl-1,3-di-(2-chloroethyl) hydantoin; 5,5-diphenyl-3-(2-bromoethyl) hydantoin; 4; 5,5-dimethyl-3-(2-chloroethyl) hydantoin; acetylaminophenol; aminobenzoic acid; maleimides; 3-di-(2-chloroethyl) hydantoin; 4-N-acetylaminophenol; 5; 5-dimethyl-1; 5-diphenyl-3-(2-bromoethyl) hydantoin; 5-dimethyl-3-(2-chloroethyl) hydantoin; p-aminobenzoic acid
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363221080065

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.